A Thank You Note To The Guy Who Told Me To Stop Putting Myself Down

Dear Sir,

Hey there, long time no see. Kidding, I saw you like a week ago, but you’re a continent away from me now, off in a country I’ll probably never visit, so it doesn’t really matter that we just hung out. Sad face.

Jon Hamm in ‘Bridesmaids’

Three weeks ago, I told my lovely, magical, patient best friend Anna that I wanted to pen a long-winded TTF article about a terrible guy who nearly destroyed me two and a half years ago. All right, I need to take some responsibility here: a guy whom I let nearly destroy me. The moral of the story, which I won’t be writing about in TTF, is that I poisoned myself by basing my value on the treatment I received from an unworthy individual. I started writing the post soon after chatting with Anna, and while I’m (kind of?) proud to say I’ve produced 3,000 words so far, it was an exhausting post to put together and I’m not even done. I walked away from the first half of draft one feeling drained, sick, ashamed, disgusted, livid, the works. In other words, it wasn’t cathartic to vent about the downright evil connection I had with a young man who loved throwing me out of his bed like a used condom and at times made me believe he didn’t care whether I lived or died. It brought me back to one of the lowest and most vulnerable points of my life, which you got a sense of during our brief but substantial interactions.

While I plan on writing about this rotten, appalling  experience someday (ideally Taylor Swift style, because look how well that always works for her), I must say that I don’t really want to be in fight or revenge mode right now, and publishing that would just resurrect the toxic energy I worked so hard to push out of my life. I’m ready to finally give my friends and TTF readers something happy to read. During darker days, Anna would say to me, “Tell me something good, Laura.”  Well, Anna is finally getting her wish (a year and a half late, but she’ll forgive me because that’s what friends and TTFers do).

Whether you like it or not, I want to talk about you — the guy who (temporarily) restored my faith in the male species, not that I’m getting carried away or putting a ton of pressure on you or anything…

Emma Stone and Ryan Gosling in ‘Crazy, Stupid, Love’

Last Friday night (thanks for the heads up, Katy Perry), my friend convinced me to stay out later than I’d planned. We’d just finished eating comfort food at Doc Watson’s Irish pub and I intended to head home, but she insisted we stop at Swig, an uptown bar where her friend worked. Though tired from the week, I accompanied her to the venue, where I ended up meeting you. I remember staring at you from across the room after I got my drink. I thought you were well dressed and had probably already found someone to spend the evening with. That’s what I assume of every guy I meet, no thanks to past experiences.

Your friend approached me before you did, but you swooped in before I could get a sense of what he was about. All I knew was that I was surrounded by five fun Australians who only had a few days left in New York. I liked your cologne, but more than anything, I was drawn to your fiery attitude. You seemed very grown up, so I wasn’t surprised to hear that your friends call you “Dad” and expected you to put together the entire itinerary for the trip (I’ve so been there). You enjoy making them happy though, and I admired that because I’m the same way with my buddies. But there weren’t just warm fuzzies between us. We started the night on a playfully combative note: you made fun of me for forgetting the name of the Sydney Opera House.

That weird thing in Syndey

“‘That weird thing in Sydney?'” you said in your accent, mimicking my admittedly horrendous description of one of your country’s major landmarks. “That would be like if I called the Statue of Liberty the Green Bitch.”

“The Statue of Liberty used to be copper,” I said, whipping out my iPhone to show you a snapshot of the monument long before it developed a different shade entirely. “The color changed overtime.”

“Interesting. We’re seeing that tomorrow. If it doesn’t rain,” you replied.

Thank you, Hunters!

It had poured nonstop all day, so I was sporting my one and only pair of rain boots. You were in awe that someone over the age of four was wearing them, as people don’t really do that in Australia (or so you told me), so you had me place my legs on your lap to study the perplexing walking instruments. You traced the red Hunter logo and rubber material, seemingly amused. I was too. I knew then that you were sold.

We continued taking swipes at each other for another hour before migrating to another bar and delving into serious topics. I laughed after you bought my drink, as the last dude I’d gone out with had failed to do the same after being an hour late to meet me on an outing he’d suggested. Such gentlemen I hang out with.

I told you about this fellow with a hint of embarrassment and you warned me never to trust French guys named Jean-Paul anyway. After I whispered that we were a few feet away from the friends of a guy who had harassed me before, you seemed angry, not at me, but for me. I didn’t want that for you, though. To lighten the mood and quit coming across as a perpetually vulnerable, inherently unlovable sad sack, I asked you to talk about your life, and thank God you did.

You’re very close with and protective of your sister, who is a year older than you are (even though you call her your little sister). You’ve watched your mom and dad remarry other people a handful of times and seem pretty unfazed by it, even though I know firsthand it’s not easy to have parental figures come and go. You’re more resilient than I am in that way. I said I’m a serious person because I’m extremely career-driven, which led you to ask whether there’s a difference between “serious” and “motivated.” We laughed and you admitted to arguing for the sake of arguing (I’m guilty of this as well), but for once, I was OK with it. I liked talking to a someone who was willing to challenge and debate me. It was a nice change from empty bar conversations I have to deal with on a regular basis. You also got mad when I said I looked like a slob, and while I definitely felt grimy and haggard from running around the wet streets of NYC all day and night, I appreciated that you forced me to quit saying that I was an awful sight. Because I’m not.

3:00 a.m. rolled around and we were still chatting at The Penrose, which was clearing out and closing, so I awkwardly invited you to follow me back to my digs, where we talked for another hour or so before getting a move on things. As we sat side-by-side on my bed and discussed my barely legible to-do list, I regretted that we hadn’t kissed at the bar, because that’s definitely something two strangers should do before retreating back to one of their residences. What if we had no chemistry? Oh well, I thought, if this turns out to be a disaster, at least I’ll have something funny to blog about.

Studying my wall, you asked about my journalism award and I explained that I’d received it as a college junior, back when I viewed myself as the biggest thing in the world for publishing a 700-word column per week. Now I write piece after piece on a daily basis, rarely having a major attachment to my work but always feeling squirmy, inadequate, overwhelmed, stifled, and behind. It’s not that I dislike what I’m doing, I’m just ready to evolve. You get that because you’ve lived your entire life on the edge. You fly military planes and can go a week without food, for God’s sake.

As much as I loved discussing my college writing accolades, I became increasingly frustrated and nervous. I didn’t want to talk about my trophies. I wanted to see whether we were compatible in another way. After all, you hadn’t come over to learn the extent of my epic nerdiness. 

Emma Stone and Ryan Gosling in ‘Crazy, Stupid, Love’

Once we finished our glasses of water, I made a beeline for the light switch, whacked it off, and pulled your face toward my own. Phew, I thought. Zero weirdness. Even so, I could tell by your classy attire, rippled six pack abs, sparkly blue eyes, head of dark hair, and perfectly-sculpted biceps that you probably get a lot more play than I do, and that made me noticeably anxious and even more frantic than usual.

“What now?” I said after we’d made our way into the sheets.

“You tell me. You’re supposed to be the older and more mature one, right?”

I sighed. “Yeah. Right.”

I’d almost forgotten you’re two years (and two months) younger than I am, and for a split second, I believed that was the reason you’d agreed to hang out with me in the first place: you didn’t know any better. There I go again. I’m always getting down on myself, mainly because the only other younger guy I’ve been with was the aforementioned putz in paragraph two. After him, I didn’t do anything — aside from endure a meaningless kiss here and there — for a year and seven months. As Olivia Wilde eloquently described her post-divorce experiences, “my vagina died.” But it was more than just my personal life that went on a hellish vacation. It was my ability to connect with others, my desire to go out and meet guys, my joie de vivre.

I don’t know whether this was obvious or not, but I did confess around 5:30 that I’d been, for the most part, out of the game and reclusive for a while. You assured me everything was fine, and when I kept saying sorry and stating that I was uncertain, you looked at me and commanded, “Stop apologizing and putting yourself down.”

People who apologize a lot reflexively say “sorry” after an order of this nature, but I simply nodded and kept that word out of my vocabulary for the duration of our encounter. Sometime before sunrise, I quit fretting and feeling self-conscious, and we covered a lot of ground. You said you loved that I’m a writer because of the way I phrase things. You like that I walk fast because you move with purpose and urgency as well. You think my past experiences with men are unfortunate, and you regret that I haven’t had any positive stories to share for five years (I promise I’ll be fine, I just have to learn to pick better). I said I envied your outdoor survival skills, which you acquired in the military. We argued about the pronunciation of “climate.” I say it like “climb-it” whereas you’re convinced it’s spoken as “climb-AT.”

I asked whether you’d heard of “The Simpsons,” and that question gave you a good laugh. I went on to say that it was quite possible that the comedy series isn’t as big a deal in your country as it is in mine because it’s based on the modern U.S. family. You assured me families are the same everywhere, which got me thinking about “Anna Karenina.”

“You’re just a trove of knowledge, aren’t you?” you said.

I shrugged. “Something like that.”

At around 6:45, you suggested we get some shut eye. You had a big day ahead and I needed to catch up on sleep after an intense work week. I found myself settling into the crook of your neck, and after five minutes, presumably when you suspected I was out cold, you kissed the top of my forehead.

The following night, you sent me a Facebook message about your Saturday excursions with the guys.

“How was the Green Bitch?” I asked.

“The Green Bitch was good. Took a while to get out there but it was pretty good. I am about to lose my rights to the laptop so text me 😉 (310) xxx-xxxx”

And so I did, and we had our last hurrah the following day after several hours of texting and joking around. You fell asleep on your cab ride back from the Giants stadium, and I light-heartedly told you that you’d need your rest prior to our shenanigans.

“You’re not going to try to kill me again, are you?” you said.

Unfortunately not, as I was plagued with foot and leg cramps, prompting me to tell you it was because you were dealing with a senior citizen. We hung out at the Times Square Westin, where I’d stayed during my high school drama trip eight years earlier. I hugged you goodbye but was at a loss for words as I usually am with formalities and farewells, and that was it.

You’re out of my life and we’re not going to remember much about each other ten years from now. You’ll reflect on your month-long vacation to the states and gush about the hilarious times you had with your friends. I won’t be able to identify you by name, but I will remember the strong-willed, humorous, opinionated Australian who convinced me I deserved much more than I’d ever gotten, so thank you. I hope I gave you more than just a funny travel story about a neurotic redheaded Californian who kept you up all night.

That Dreaded and Dreamed-of First

Editor’s note: This is the sixth installment in a series about losing one’s virginity, inspired by this project from Rookie magazine. Earlier authors include JessKate, GinaAnna, and Heather. It’s not explicit, but probably not for the easily scandalized, like the author’s parents…

During my freshmen year at college, fairly early in the term, I was at dinner with a group of my new friends. We sat around our — I want to say it was Indian — food and chatted about whatever was on our minds. Since I was with five guys, the conversation, unsurprisingly, was about sex. Specifically, it was about in how many states they were no longer virgins. I, being a virgin in every state, didn’t speak up. Finally, I couldn’t be tactfully sidestepped any longer. “How about you?” I didn’t know what to say. “Um?” Luckily one of the guys there that night came to my rescue and diverted attention away from me. The evening proceeded unmarred by my inexperience.

Except the whole situation stuck with me. I’m not used to having nothing to add to conversations. As we walked home that night, just my savior, another close friend and myself, I couldn’t help but bring it up again. Somehow during the walk it was decided that when I did — and none of us doubted that I would — lose my virginity, my savior would be the first person on the list of people to text about it. Like right, right afterwards.

Maybe you noticed, and maybe having a list of people to update afterwords gave it away, but I was not ready for sex at 18. I wasn’t waiting for anything or even anyone in particular. But I wasn’t willing to jump into bed with just anyone. I was content to be a virgin; yet  another sign that I wasn’t ready.

Queen Elizabeth I, the Virgin Queen – I would not have been okay with that nick-name…

Only, I wasn’t content being a known virgin. A few months later, 19 now but still virginal, my coworkers, both of whom were older and infinitely cooler than I was, were complaining about the dry spells they were stuck in. “Don’t,” they warned me, “have sex until you have some regular partner, because the in between is horrible.”

“What?” I protested my status as virgin, “but, I’m not…” How had they known? Was it stamped on my forehead, written there with red lipstick?

“Also,” one cautioned, “don’t lose it with some guy you don’t know.” Nothing like walking out of a frat house without so much as a goodbye to make you feel like a whore, she recalled of her first time. “But,” the other reasoned, “don’t think it means you’ll be in love after.” He remembered crying and telling his partner how much he loved her right after. It didn’t end well.

Suffice it to say, I was ready for the shift to end.

I remained — mostly because of my friends: the biggest adoptive family, who had all decided I was America’s Little Sister — a virgin for the next 2 years. And finally was ready. But I was still single. And generally not much of a partyer. And altogether unsure of how it would just happen. I am a goal setter, so I set my goal: lose my virginity before I turn 22. All I needed was the guy.

Whom I met at work. I liked him from the moment I met him, even engaging him in some of my most classic awkward flirting. For over a year, nothing happened. As much as I initially liked him and continued to like him, I liked pretty much every other guy in “the office” just a little more. It was awful of me, but he was my back burner guy, the one I went to when no one else was responding to my texts. But slowly, and after a few disappointments with the others, the back burner became my only burner. And I was okay with that. He was sweet and silly and good to me, what wasn’t to like? He also had all the right appendages to satisfy my goal. It was November – my birthday was only four months away. It was time to act.

It started as a Facebook chat session while I wrote an essay that turned into a midnight Taco Bell run. Don’t worry, it gets classier. It was midnight. On a Wednesday. And I was in a man’s apartment. We both knew why I was there.

But instead of getting down to it, we started a movie. Road House. Not an amazing film, but not the worst thing to get buzzed to — buzzed enough to not mind when yawning stretches turned into cupped breasts. I think my fondest memory of the whole night was when, partially undressed, he carried me to his bedroom. Still in the fairy tale, and under the influence of alcohol, it happened: The first penetration. I had a moment of clarity, the same I have every time I realize I’ve achieved a goal, before I relinquised all emotion to the experience.

Which, frankly, went on for far too long. He was significantly more experienced that I was and while he was charitable to my general ineptitude, he also was determined to get what he wanted out of me. Long before he’d finished I was composing the text that’d need to go out. Besides, I had school in the morning and was pretty ready to go to sleep.

“Well,” I said when it was over, gathering my underwear and putting my clothes on, “it was nice to see you.” And then I left. I checked off my virginity both with a goodbye (of sorts) and without saying I love you. I didn’t even wait to get out of his apartment to send my victory text.

Onward to Happily Ever After

For months and months and months, I’ve liked this boy. You’ve probably read about it before on Serving Tea To Friends. You may be tired of hearing about it. In fact, I realized that I was getting tired of hearing about it. What was I still thinking about him for? Why was I going over and over what might be if I’d just do something? I promised myself that I’d say something, knowing full well that I’d kept my fingers crossed behind my own back. I was a champion of finding an excuse not to say or do something when we two star-crossed lovers were together. And I say ‘star-crossed’ because we do both love the stars; and surely, I thought, that love could transfer to me, made up as I am, at the most basic level, of stars.

So I never did anything but hope that it would just happen; I could work out the math later. But space science isn’t like that. And neither is love. And I probably wouldn’t have ever said anything, except Lyzi posted about what we would do if we weren’t afraid to do it. She challenged those of us in the Serving Tea To Friends community to live better, fuller lives for just one month, then report back on facing our fears.

I don’t think I would have said I was afraid to tell the someone that I liked that I liked him. I find no shame in the way I feel. But I was concerned that I’d make him uncomfortable. Or that, in an effort to prevent awkwardness, be awkward or even mean. And there was that dark unknown I had to face: what if he doesn’t like me? It was not only a possibility, but after such a long time of not dating, a real probability. If I was afraid of anything, it was how I would react to that.

But Lyzi said, seemingly directly to me, “Is it telling a romantic interest how you feel? Write him a letter. Think of all the things you could do if you weren’t afraid.” So that very night, I wrote him a letter.

Well, I wrote him an email, it being the 21st century and all.

“I really like that you like all the same things I like. And I really like how easy it is for me to talk to you, I don’t know how to explain it really, but with everyone else I am never quite sure how much they know about history/science/whatever, but we seem to be on the same level. I think. I like your friendship. [My brother] says that liking that you like all the same things I like is the same as flat out liking you. I do care very much about you and thought it was time that I said something.”

And now it is time for the updates: Sorry, dear readers, to let you down, but he doesn’t feel the same way. I know it isn’t the romantic comedy ending we were all hoping for, me more than anyone else, but it is the ending we got. He doesn’t, in so many words, like me.

The fears that I had have not reared their ugly heads. I am not devastated by the news. In fact, I am relieved. Maybe I knew all along, but hope wouldn’t let me acknowledge that truth. I finally have permission to like other people without cheating on my Tucson-based crush. And I think the friendship I still share with my ex-crush is stronger. At least, I feel better about it. All in all, I am happier for having said something.

Not everything is rainbows and kittens. Yes, I am happy. Yes, it was the right thing to do. But also, yes, I miss the imaginary life I built on morning commutes and day-dreamt afternoons. I still, for all the respect I have for his feelings and all the faith I have that I will find someone more perfect, think of him as the most compatible person for me that I have met to date (Pun?). I find myself ramming, full steam, into the immortal words of Sugar: “You cannot convince people to love you. This is an absolute rule. No one will ever give you love because you want him or her to give it. Real love moves freely in both directions. Don’t waste your time on anything else.” And bouncing off them.

There. You are updated. The boy who loves the stars back in Tucson isn’t the boy for me. I am okay with that. I am beyond glad that I faced my fears at long last. But I am in mourning nonetheless for the relationship that could have been. And scared all over again about the uncertainty of not knowing who the one is. But rather than fight that fear or bemoan the loss of perceived love, I will follow some other advice, “There are times, at least for now,when we must be content to love the questions.” -Neil deGrasse Tyson.

And that is a challenge I encourage everyone to accept.

On First Love and First Loss

Editor’s note: This post is part of a series about losing your virginity. This series was inspired by this Rookie Mag post. We hope it offers a glimpse at the experience of losing your virginity and all the complexities that come along with that. These pieces have hints of the explicit and are not for the easily offended.

I could write a post for you all about what it was like to lose my virginity, at 16, to the then-boy (though I thought man) I was sure I’d spend the rest of my life with.

I could tell you the details I remember. They are few, but stark: The green underwear I was wearing, which had an embroidered goldfish on the front. The bedroom, its captain’s bed, its navy sheets, its elaborate videogame setup and custom-built computer – trappings of a smart and spoiled boy.

But I don’t think I can write that post for you. I think that first, I have to tell you it’s hard when the person you want to eviscerate on the glowing screen in front of you has grown into a person you love and respect, a person you once wanted to hurt more than you had ever wanted anything in your short life, and whom you now want to protect and show charity and, hardest of all, forgiveness. It’s also hard when you know he’s reading this (hello, friend) and will wince with recognition at the above description of the fish underpants, which he once loved. You remember.

I have to also tell you that it’s complicated when that person you now, bafflingly and almost magically, want to protect, broke your heart into so many pieces you’re still finding them, in the wash, ground into the pulp you sweep from your floor, several homes removed, in the essays you try to write about love and sex and forgiveness. He shattered you, and most of the reason you don’t remember that momentous (or, in your hazy recollection, decidedly lackluster) occasion is that you’ve blocked huge swaths of your life with him out.

I want to tell you that I remember our first kiss better than I remember typing the above paragraph. We were in seventh grade, and our blossoming love had thus far been played out over AOL Instant Messenger, where we sent each other frantic and hot-handed messages of desire, punctuated with emoticons (so many emoticons) and the bad spelling that tries but fails to mask good, true, gut-wrenching feeling: “Luv ya.” He rode his red BMX bike to my house. I met him around the corner, wearing a navy tank top spangled with rhinestones and bell-bottomed blue jeans. He had on a yellow baseball cap which, my God, I can picture so clearly it aches. We talked, shyly. He gave me some gum. He said he had to go home. Someone leaned forward – was it me? – and we kissed, like people who knew what they were doing, from a place of great want and great maturity and great feeling. It was possibly the best first kiss in the history of great, doomed love. It was epic. He rode his bike home without touching the handlebars, arms held above his head in triumph, whooping. I know because he told me. This, you guys, was young love, but it was big love.

I want to tell you that, considering how young I was when I “Lost It,” as the kids (used to) say, we talked about it a lot, and we moved slow. Remember, we began our hot and heavy journey in the seventh grade, and this was not a slow burn. The wait was excruciating, but in the meantime, we did, as the kids also say, “other stuff.” We were good at other stuff. We lived for other stuff. I know I’ll regret writing this the second I’m a parent and have to imagine the hormones coursing through my own 13-year-old progeny, but really, 13 is the best age for other stuff. Remember how BIG everything felt at 13? Remember how raw all your nerves were, how sensitive every receptor, how the world began and ended several times a day, how great and big and wide and gaping and real you felt all the time? Now, imagine that as a physical sensation, as new and unbelievable pleasure. Yeah, it ruled.

I want to say that considering all the incredibly vivid memories I have of that kiss, of that other stuff, it’s weird how little I recall of that first time. I remember feeling brave, and weird, and vulnerable, and opened up, and safe, and beloved, and weird again. I remember not telling anyone for months because slut shaming has been alive and well at least since I was 16 and it was not something my friends were participating in yet, and then I remember the first person I told was my Orthodox, Hasidic Jewish best friend who was not even allowed to touch people of the opposite sex, but she was so ridiculously cool about it, for which I thank her and love her to this day. I remember other times, and I remember feeling more and more physically rejected as our relationship deteriorated. I remember being called fat. I remember going to sleep alone on a trip to Paris, and crying and crying at the vast distance between us in the tiny bed in the tiny hostel with a view to the glittering Eiffel Tower. I remember when I knew it was someone else, and I remember vividly, sickeningly, the first time I pictured them together, the little sigh he always let out as he vanished into a kiss, the sparkle of his very very green eyes.

What I want to tell you about today, here, now, you and also You, is not about first sex but about first love. I want to tell you how it brands you, how it scorches, how it, the good kind and the bad kind, which are one and the same, stays with you for the rest of your life. I want to tell you love is vast and important and impossible, and I want to tell you I have felt that, I have been eaten alive by that, and I have survived it. I want to tell you to kiss deeply and fuck passionately and say I love you through your tears and roar and roll your eyes and gnash your teeth with love, whether first or tenth or last, because it is powerful and necessary and dangerous and fucking PURE. I want to tell you that losing my virginity to the man who would break my heart is something that hurts every day, but something I will never regret.

It is Valuable Because it is Yours: On Firsts

New Year’s Eve, age 13

Editor’s note: This is the fourth installment in a series about losing one’s virginity, inspired by this project from Rookie magazine. Earlier authors include Jess, Kate, and Gina. It’s not explicit, but probably not for the easily scandalized.

What is the perfect way to lose your virginity? Every idea about it is soaked in a long history of men deciding womens’ lives for them. It’s perfectly respectable to make a personal choice to wait until one is in a serious romantic relationship to first have sex, but often the sanctity of that choice goes unexamined. What’s the right way to do it? And when?

I have felt like I was behind in my romantic life since I was about 11. One New Year’s Eve, when I was not much older than that, my friends and I tucked resolutions into boxes we’d decorated with puffy paint and sequins. Among other vows I made for myself at that kitchen table splayed with sparkles and craft glue, I wrote this: “This year, I will be kissed.”

It didn’t happen for me that year, or any of the next eight, and I wasn’t happy about it.  I was 21 when I finally fulfilled that wish, with a man who pressed me against an adobe wall and took my face in his hands. Whiskey was involved, but laughter was too.

Unlike all the times I’d tried to plan to kiss someone, all the parties I’d scanned eagerly, the spin-the-bottle games I avoided,  or the friends of friends I’d tried to coquettishly impress, it wasn’t difficult or fraught. After all the agonized journal entries about how awful and stunted I felt because I finished three and a half years of college before sharing a kiss, it felt like the easiest thing. Though we never dated or were even really friends, I am proud that man was the first one I kissed.

Though some might think having this story out there could hurt my job prospects or be more than a little too much information, here is why I’m writing this: Because my twelve-year-old self needs to hear this. My sixteen- and eighteen- and twenty-year-old selves need to hear this. Maybe there are some girls out there like me who need to hear this. And here it is:

There is no perfect or correct way to first experience physical intimacy. There are a lot of painful and dangerous ways, but as long as you know and can protect your own body, have no shame. If you’re sixteen or twenty-one or sixty-one when you first open your mouth against someone else’s, that experience is true and real and legitimate, because it is yours.

It doesn’t matter that the average age to first kiss or fuck is years younger than you are – you are not an average. Seventeen magazine doesn’t hold the compass to your realest life. Those girls at summer camp who make you feel inadequate, to whom you lie about how many boys you’ve kissed? They don’t hold your map. The raspy-voiced girls when you are in college, the ones who casually mention their genital piercings, they have nothing to do with your timeline. They can’t say what is right. Only you can.

I first had sex less than a month after I first kissed a person on the mouth. He wore flannel and played guitar, and we met because the man I’d kissed introduced us. On the patio of that college bar, we clinked glasses and talked about the books we both loved. I was a literature major and he taught ninth-grade English, and we both loved David Foster Wallace and Catcher in the Rye. He was visiting from New Jersey for the weekend. When he left that patio I got a text: “Not every day you meet a girl who drinks whiskey and has read Infinite Jest, so I got your number from my friend. Come out with us tomorrow?” He didn’t seem like a phony.

It wasn’t a romance, and it wasn’t a transaction. It was, for me, a decision made sober and without apology. There was mutual attraction, he was smart and took me seriously. He was leaving in two days and I never had to see him again. The next night, when I took his hand at the Sonoran hot dog stand and asked him to walk me home, it was without hesitation. The day of texting we’d done about music and literature and cosmic dissonance was all the relationship I wanted or needed from him.

He didn’t know it was my first sexual experience, and I wasn’t going to tell him. Years before I had decided a penis wasn’t the ideal instrument for breaking flesh, so he didn’t have to know. He was a weird, stiff-tongued kisser, and not as good with his hands as I expected of a guitar player. Perhaps it wasn’t what I would have called the ideal, at fifteen or seventeen. But here is what I have to tell those younger desperate selves:

One day when you are twenty-one and tremendously unkissed, it will not be the end of you. Do not lament the days you thought you were the last virgin alive. One day a man who loves books like you do will unbutton his flannel against you and you will be proud to have him between your legs. Never feel like a failure, never feel like less than a woman, because of your sexual experience.

To that fifteen-year-old self, you are not better than your friends because you think you are above sexual urges. To that seventeen-year-old self, you will still have a superlative college experience though you are a tight ball of anxiety about your experience with men. It isn’t a penis you’re searching for, in those hours when it feels like no one will ever take an interest in your lips.

When it was over, it wasn’t really pleasure I felt. It wasn’t love or ecstasy, and it wasn’t pain or regret.  What it felt like was relief, a great unspooling of so many expectations I had of myself, all wound so tightly around a knot of nervousness and shame. It felt like release.

Inviting that man to walk me home and into sexual experience was perhaps not the perfect way to lose my virginity. But it was this: Authentic. Free. Mine.

Planning for Success: A Virgin Story

Editor’s note: This post is part of a series about losing your virginity. This series was inspired by this Rookie Mag post. We hope it offers a glimpse at the experience of losing your virginity and all the complexities that come along with that. These pieces have hints of the explicit and are not for the easily offended.

This post, in particular, is not safe for work.

If there is one thing that Myers-Briggs got right about me it’s that I am a judger. I organize; I structure; I plan. At any point in my life I can tell you what my schedule is for the next five minutes or the next five years. I value knowing what’s coming and being in control of my circumstances. Having a solid plan under your belt—not to mention several contingencies— is my recipe for success.

Planning takes brainpower. You gotta consider the costs and benefits of any particular action. When I was younger, the risks of sex far outweighed any potential benefits. Growing up, I watched more than one of my friends get pregnant and drop out of school, perform a “home made” abortion, or contract an STI. Who knows what my parents would have done if I’d gotten pregnant? To top it all off, everything I heard about having sex, from my mother and my friends, made it sound pretty awful, particularly if you had to sneak around.No. At 15, sex wasn’t even on my agenda. No marriage. No sex. Ever.

But even the best made plans need to be flexible. By the time I hit 18, my priorities changed. Risks went down and benefits went up. Not only was I ready for sex, I was impatient for it. I even tossed around the idea of having my high school ex-boyfriend fly across the country to help me out. Oh, yeah. I wanted it bad.

Ultimately, though, there were still risk factors to mitigate. I needed someone who I could trust, was able to stick around, and invested enough to help me through whatever psychological issues I was expecting to have. Planning requires patience. I quelled my impulses, slid sex into the schedule, and waited.

Har. See what I did there?

So I walked my virgin self to a fraternity at Georgia Tech. There, a shy nerdy man with shoulder-length dreadlocks, a lean build, and the most beautiful brown skin I had ever laid eyes on expressed his interest in me. He was quiet, observant, and jaded—my opposite, on the surface. He spent the night on our second date, but before any “funny business” happened, I laid down the facts: Not only was I a virgin, but I had never had my breasts fondled, never given a blowjob, never received oral, or, pretty much, ever been naked in a room with another man. I wasn’t just a virgin; I was Supervirgin, and I had no intention of significantly changing my state that evening. He and I crossed the first experience off of my list before cuddling up to watch a movie and falling asleep.

After agreeing that we wanted to pursue a relationship, we made a plan: No intercourse for three months. He needed to build trust as much as I did.

For three months, he and I explored corners of our sexualities with the full understanding that we didn’t have to have intercourse to be intimate. I cried the first time I gave him a blowjob because I got frustrated and my mouth was sore.  Cunnilingus was a lot messier than I had expected. In the meantime, we made all the preparations: He went and got tested for STIs; I schluffed over to an OBGYN and got a diaphragm. Together, we crossed off all the items on my “to-do” list, and even found a few more things that I hadn’t even considered doing before, all without inserting a penis into a vagina.

I am, however, also a stickler for deadlines.

Don’t get me wrong. I was having fun, but by the time our three-month marker came up, “impatient” would have been a mild word to describe me. I was ready to get ‘er done, even if I was so nervous that he felt the need to give me a full body massage before the foreplay even started. My impatience might have been the cause of our less-than-adequate plan. We didn’t really think out what position beforehand, and that’s where the trouble began.

Missionary hurt. It burned. Like someone was stretching my skin past where it was supposed to go. I tensed, he backed off. Rinse and repeat until I was so aroused and frustrated and confused that I started to cry. He lay down next to me and pulled me into his arms, telling me that we could stop for now and try later.

Um, fuck no. I hadn’t put up with three months of perpetual foreplay with the hottest guy I had ever dated to give up because I had forgotten to work out a few steps. Sometimes, a little improvisation goes a long way. I flipped myself on top of him and positioned my partner’s half-slackened penis where it felt right, determined. This time, I had control. This time, it felt better. Before I knew it, the burning sensation was just one more feeling flooding my body, giving an edge to the satisfaction as we inched closer and closer to full insertion. Eventually our hips touched, and we smiled.

My mother once advised me that my first time would be awful. She said it would be awkward, painful, and traumatizing. I shouldn’t  expect to enjoy it. Out of all the things I have proven my mother wrong about in my life, I think this is my favorite. My partner panted in time with me as I moved, tentatively at first, then boldly. I moaned. Loudly. His housemates teased me for it afterwards, but it was worth it. To this day, the sound of my partner murmuring “Oh, I think she likes it” in my ear that night is the most erotic thing I have ever heard.

I announced my lack of virginity to the world the next day by leaving a group on Facebook called “The Sexy Virgins,” and I updated my status to say “Gina Luttrell is a little sore.” I wasn’t ashamed to announce it. Having sex was never a shameful thing to me. I planned; I followed through; I got an amazing return. Who wouldn’t be proud of that? I didn’t lose my virginity. I put it aside, proudly, unabashedly, and without regret, because the next section of the agenda was beginning.

Of Condoms, Gravity, and Love

Editor’s note: This post is from a series about losing your virginity. This series was inspired by this Rookie Mag post. We hope it offers a glimpse at the experience of losing your virginity and all the complexities that come along with that. These pieces have hints of the explicit and are not for the easily offended.

Losing my virginity was an incredibly normal event. My Mom taking me to church to tell me that Santa Clause wasn’t real was a more traumatic affair (“WHAT ABOUT THE TOOTH FAIRY?!” was my overly-loud response from the back of the pews). Getting Beanie Babies as gifts after I scored goals in my childhood soccer games was more fulfilling than my first bedpost notch—Scottie the Scottish Terrier was my first (Beanie Baby, that is). In fact, I anticipated writing the follow-up romantic email to my boyfriend MORE than the sex that necessitated the email.

Losing my virginity was, in a word, boring. I was at my boyfriend’s house and it was summer time. At that point, we’d been together maybe about eight months and were, of course, in love. I didn’t know anything about anything when it came to sex except that there should be a condom, the girl goes on top (because gravity “helps keep those suckers down”), and that you have to be in love. We didn’t know to check the expiration date of the condom (a moot issue in the end, as even if wasn’t expired, the latex was probably warped from sitting in the glove box of his car during Phoenix summers). I was 15 and had seen enough in my Cosmo magazines about the wiley ways of the “cowgirl.” And we were, of course, eversomuch in love.

Anyway, it was summer, we had a condom, we were in love, and I got on top. I knew it would hurt because I had done my research. It always hurt the girl and it was always ecstatic for the boy (thank you, Cosmo). I didn’t expect it to hurt the way it did, though. I felt nauseated: no sharp pain, no hemorrhaging, no ripping. In fact, I became very nervous that I might throw up on him and my palms got very, very clammy. So clammy that I slipped and nearly cracked his chest open with my skull. Risking physics, we switched positions and he got on top. That’s when I learned that methodical, rocking movements also nauseate me.

Suffice it to say, it was a very short affair and I am now the victim of motion sickness and varying degrees of vertigo. I don’t know if having sex during high school, having sex when I was young, or having sex when I wasn’t mature enough messed around with my relationships. I have always wondered how my boyfriend remembers it—how any of the boyfriends whose V-cards I swiped remembered their first times with me. I wonder if it hurt for them, if they wanted to throw up.

I am proud to say that the sexy times has turned into a much more pleasant experience, and continues to be so as I learn more facts about keeping my body healthy. I delight in having “the talk” with my partners about what our game plan would be if the shit hits the fan (embryo-formation wise). I like learning about new contraceptives (someday, male BCP, someday), ways to detect STD’s (did you know that trichomoniasis looks like the foam from your Starbucks lattes?), and being so completely comfortable with someone that we can talk about preventative measures, testing dates, and sexual health.

You will never look at this the same way

I wish I had known – REALLY known – what sex appeal meant when I was 15, but I guess I needed the adventures to experience the follow-up.

This One Time, When I Was a Virgin …

Editor’s note: This post serves as, hopefully, the first in a series about losing your virginity. This series was inspired by this Rookie Mag post. We hope it offers a glimpse at the experience of losing your virginity and all the complexities that come along with that. These pieces have hints of the explicit and are not for the easily offended.

When I was in high school, I hung out with a pretty sheltered group of kids. We were the theatre and band kids, and not the sexually active kind. I was a lot more promiscuous than I ever told any of them. When asked the question “Will you wait until you are married to have sex?” I, like the realist I’ve always been, said, “Gosh, that sounds like a lovely and romantic thing to do, but I don’t think it’s a realistic expectation to put on myself.” This was appalling to most of the people I hung out with because abstinence-only education taught my friends and me that sex before marriage would lead to an inevitable STD upon first penetration.

The other thing that separated me from my friends and their sexual journeys was this huge secret I was keeping. I was feeling the feels for my best friend, and, oh yeah, she was a lady. It was one more complication on top of all the talk of boyfriends and losing your virginity. The desire I felt strongest, and still feel today, was this yearning for a connection with someone. I wanted so badly to fit in with that image of being in high school with a boyfriend and exploring bodies in an innocent high school way, but that wasn’t meant to be my story.

In my pursuit of this partner, I took to the only social media outlet available to me as a senior in high school: MySpace. The ultimate resource for everything from booty calls to all those STDs I mentioned earlier. I went out with about a dozen guys, trying to explore my sexuality and understand why I always felt so different from my female peers. I had some pretty terrible dates and admittedly put myself in some dangerous situations because meeting people on the internet in 2005 was not ideal. This is where I met the guy who would take my virginity.

His name was Oliver, which was so charming to me, and he was a red-headed scrawny college guy. We had chatted for a few weeks until he was in town from his fabulous college life to visit with his parents, so we seized the opportunity to meet in person for the first time.

I don’t recall going into this date with the intention of losing my virginity, but that’s how it went. We met in the Safeway parking lot because I like to keep things classy. He went in to buy us alcohol while I waited in the car, which was so cool to my 18-year-old self. He came out with the only thing I could suggest he grab: Smirnoff Ice, the high schoolers’ go-to adult beverage. Then we drove out to the middle of the desert for some privacy, lively banter, and booze.

Now, I know what you are thinking: “Jess. Are you telling me that you drove out to the desert in the middle of the night with a stranger and a six pack of Smirnoff Ice on purpose? Did that not strike you as a potentially bad thing to do?” Frankly, no. It sounded like a dangerous thing to do, but I was looking for that experience.

What began in that Safeway parking lot was hardly the safest way to go about losing my virginity, but Oliver was really a nice guy. He didn’t come with expectations. Up until that point, I’d never had more than a glass of wine at my cousin’s wedding, so three Smirnoff Ices put me well over my limit. We talked in the front seat of my car, and he suggested we move to the back. I knew what that meant, and recall feeling ready for it. There wasn’t much to talk about once we positioned ourselves in the backseat of my car. I don’t think there was a discussion of the status of my virginity, but by the end of the night, it was unquestionably out the window of the claustrophobic backseat of my Honda Civic.

Looking back on this experience, I can honestly say I have no regrets. The loss of that virginity felt inconsequential compared to the first time I slept with a woman. It was a test, an answer to some questions. So, why wouldn’t I just consider the first time I slept with a woman to be my actual “first time?”

First times are a hard thing to decipher when you are challenging the norms of sexuallity. I may technically have two sets of first times, but the actual first time was the first time I took my clothes off in front of someone else. It was the first time someone attempted to please me. It was the first time I made myself vulnerable sexually to another person. Regardless of his gender, this was my “first time,” and I’ll always remember it as such.

Of Bikes and Boys

Remember several months ago when I wrote about having a crush? Oh, those bygone days of yore. Five months, several not-dates, and a whole self-help section of advice from my friends, and I’m still in love with him and he still either has no idea or no interest. But what I’m holding out for is that he is just as scared to say something as I am. There’s a word for that in some dead language from, like, the very tip of South America that means the exact same thing. I haven’t done the math, but I think that means that maybe, just maybe, I’m right, he feels the same, and I just haven’t pulled enough petals off of daisies.

My friends, on the other hand, don’t see the correlation. They reference He’s Just Not That Into You, promise that there are plenty of fish in the sea, and point out I’ve moved 2,641 miles away from him.

I’d like to remind the home audience that that isn’t the point. The point is, for some ridiculous reason, I am head over heels for this guy and no matter how many other fish there are in the sea, I’m kinda over fishing. Besides, I’m clearly not all that good at it.

Let me explain it this way: Recently I was on the hunt for a bike to get me around my new haunts, and a bike is a perfect metaphor for this guy, let’s call him Todd, because he loves bikes. When I started my search, I made a list of what I wanted in a bike: used to the point that is had some character but not to the point that I’d need to do a lot of work on it, a hybrid: something with a light frame like a road bike but with a heavier tire and upright handle bars, in my budget, and, of course, I had to be attracted to it. After a few weeks of craigslisting, falling for the next best bike, maybe pining for one I missed out on, I saw it. A dopey bike from the 70’s that just needed a little love and some down hills to get it going again. It fit the criteria and was within reach. I was in love.

Even before I got the bike, some part of my brain (and my mom), had their doubts. Is this the best bike for me? Is it going to give me everything I need from it? Is it going to require more than I want to put into it? How, you dolt, can you be in love with something that isn’t even yours yet?

See how this is a perfect metaphor? For the one I also have a list of requirements: someone with character and history but not baggage, someone who can communicate with my friends and family thoughtfully but who I can talk to for hours about the latest from the Mars Rover (or other nerdy pursuits), someone in my age group, and, of course, I have to be attracted to him.

My friends (and mom) remind me to add “someone who loves me” to the list. And, unfortunately, probably take Todd out of the running.

“Um. No, thank you,” my dear, sweet, delusional heart says. “My list is fine. My list needs no editing. My list has been fulfilled, why in the world would I change that?”

“Yes, why indeed?” My brain, who is doing it’s best to stay out of the mess altogether, muses distractedly. “Wouldn’t want to change the status quo. Because, let me guess, ‘This way we can’t get hurt, at least.’ ”

Which just leaves me, alone, anthropomorphizing my vital organs to argue, “Hey, I did get that bike.”