How to Lose Your V-Card as Gracefully as Possible

Pin it

Ryan O’Connell is a New York-based writer. He likes shoegaze, the Olsen Twins, and figuring out why people do the things they do. Oh, and he tweetsCheck back each Thursday for his latest Call Your Boyfriend column. (You KNOW you have a question. Send it to Ryan.)

Dear Ryan,

I’m 23 and during the past year I’ve had to confront that I’m essentially gay (a drawn-out, tortured process featuring many angsty diary entries). I’ve never gone beyond kissing someone, and I’ve never been in a relationship, which is a locus of intense embarrassment for me. I want my first time to be with someone who I feel I can trust enough to be patient and non-judgmental. More than that though, I’m just scared. I’ve given up two chances at sloppy drunk hookups with hot guys because I felt self-conscious about my body and was terrified I’d do something wrong if I went home with them.

More than wanting sexual experience, I’m lonely. I have a fulfilling life in terms of work and friendships, but I feel like there’s this hole in my life since I don’t have a boyfriend. Over the last few months, I’ve gotten much more confident about chatting up guys, but nothing seems to lead anywhere. I overcome my shyness and put myself out there, we go on two or three dates, which seem to go well, then…nothing. They either blow me off or say that they’re busy or the timing is bad. I always internalize this and feel that I’m not good enough for anyone. I feel physically ugly and I obsess about things I might have said to put the guy off (I’m a book geek who says things like “locus of intense embarrassment”). This just happened a week and a half ago with a guy I really liked and I can’t stop thinking about him.

Sometimes I feel like it’s not even worth trying any more, and I should just move to Tibet to become a monk. What am I doing wrong? How can I cope with being made to feel inadequate? How should I address the virginity problem? Help me babe!

-V for Virgin

Hey honey,

Reading this felt like someone was reaching into my chest, ripping out my heart, and playing a game of hot potato with it. I FEEL YOU, GIRL. I feel all the feels of this question. Everything you expressed is something every gay man — hell, every PERSON — has felt at one point.

Let me give you a little bit of my romantic history for a second. I came out of the closet when I was 17, and basically had a gay pride parade waiting for me on the other end. My family and friends were all obsessed with me being out, and showered me with love and attention. I even threw a coming-out party complete with gift bags full of penis pasta and dildos. Seriously. It was insane.

Then, shortly thereafter, I fell in teen love with a boy and lost my virginity. The whole thing felt like a dream. My main fear about being out was that I was convinced no guy would ever love me. I didn’t have a gym body and I wasn’t drop dead gorgeous so I assumed that meant I was doomed to a life of celibacy. When that didn’t end up being true, when I ended up getting laid by someone I actually liked, I was stunned. Like, I actually couldn’t believe another guy wanted to see me naked and do things with my penis. Sometimes I still can’t (which is something I definitely need to work on).

I wish I could tell you that I don’t have insecure thoughts about my body, but that’s just not true, for me, or for anyone. Learning to love yourself is an ongoing process. Sometimes it’s one step forward, two steps back.

When I went away to college, I backslid with my self-esteem and became accidentally celibate for a year and a half. That was extremely hard because I felt like I had conquered all of my issues but, of course, when I became single again, all of the awful thoughts I had about myself were waiting for me. Today I am 26, I’ve been out for nearly a decade, and I have periods when I have lots of sex and I have periods when I have nothing. The inconsistency is difficult. Giving into the “I’m ugly and undesirable” thoughts is far too easy. I wish I could tell you that I have it all figured out and that I don’t have insecure thoughts about my body, but that’s just not true, for me, or for anyone. Learning to love yourself is an ongoing process. Sometimes it’s one step forward, two steps back.

So really, my advice to you is that it just takes time, and there is nothing wrong with your situation (or with you, for that matter). You being a 23-year-old virgin is more common than you think. In fact, one of my friends who is a chic, stylish hunk of man just lost his gay V a few weeks ago, and he’s in his late twenties. It’s particularly hard for gays because people think that gay men are running around and having all this sex, but that’s not always the case. I’m friends with some gorgeous gay boys, the kind who you’d think have no issues getting laid and getting into a relationship, and they’ve all been where you are.

No one is invincible to those kinds of feelings. Just be patient, continue dating, don’t close yourself off, and the rest will come.


To start, this is all kind of embarrassing: I’m in a sexless relationship, so I decided to go elsewhere to meet my needs. I met this guy on a sex site, he’s single and knows my situation. We’ve gotten together a few times now, and it’s absolutely the best sex I have ever had. He says the same. (But I’m sure most men say that.) Anyways, I’m really starting to catch feelings for this guy and I think he wants more at times, and then at other times I’m not sure. He wants me to spend the night and take me out to dinner. We have talked every day since we first met, but it seems to be less and less, with me having to send the first text of the day. I don’t want to come off as clingy — should I not text him and see if he texts me first? Do I tell him I really like him more then just a hook up? I don’t think he’s seeing anyone else — actually I’m pretty sure he isn’t — but do I even have the right to ask, seeing as I’m in a relationship? Also he’s a dirty talker in bed, I’ve never really been good at that, any tips there?

Here’s a dirty talk tip for you: whisper “I have a boyfriend and I really shouldn’t be in bed with you right now.” Look, I sympathize that you’re in a sexless relationship, but you SHOULD NOT be throwing yourself into another romantic endeavor until you’ve gotten out of your current one. Babe, no offense, but it’s crazy that you’re getting involved with someone else and don’t even think about the fact that you’re, um, currently taken. Perhaps this guy is not being too gung-ho about getting into contact with you because he knows you ALREADY HAVE A BF. I mean, how much can you invest in someone when you know they have their foot in another door?


Hi Ryan,

I casually dated a guy for several months – very casual, as in, we would see each other maybe once every few weeks, and never got past a good-bye hug. I didn’t feel any sparks with him, but it seemed like he was interested in me. He always paid for our dates, was very nice and respectful and would actually call me (!!) but I just wasn’t feeling it. Now I’m seeing someone else, and this guy is still texting me and asking me out. I’ve made excuses the past three times he’s asked me, and I never text him except to respond, but he doesn’t seem to be getting the hint. I don’t want to be one of those assholes who ignores your calls/texts and never speaks to you again, since he didn’t do anything to deserve it. But how can I tell him I’m not interested in the nicest and least awkward way possible? Thanks!

Hey sweets,

Send him this text: “Hey [insert poor guy’s name here]. I’m sorry I’ve been out of touch. I’ve actually started dating someone seriously and…” Okay, shit. I actually have no idea how to send this text without seeming like an asshole. Just be honest, and kind. Good luck, hon!


Hey boyfriend,

So I got an amazing job offer in California, my dream job basically. The only catch is that my boyfriend of three years is in New York and can’t relocate. Basically my options are: take the job and lose my potential husband, or stay behind and potentially resent him for this missed opportunity. Help!

Hey Working Girl,

Ah, the almighty question of which to prioritize first: love or career? In the past year, I’ve realized that here’s no right answer to this question. It varies from person to person, relationship to relationship. Whatever you end up doing, you’re going to have some regret. You’re going to wonder the “what if’s.” No decision is easy. It’s great to have a job you love, and it’s great to be IN love.

So the big question is, right now in your life, are you more of a “love” person, or a “career” person?

I dated a bunch in college and spent my first year as a post-grad farting around and interning. Then, on my 24th birthday, I woke up unemployed with no job prospects and had a freak out. It served as a wake up call and within a few months, I had a fulltime writing job. Then, right after my 25th birthday, I got a book deal. I’m not telling you this to brag. In fact, you can use me as a cautionary tale, because the second I started achieving some success, I stopped getting laid. Seriously, I had the most love + sex action when I was an unemployed loser. WTF? Doesn’t that seem a little bit backwards? To a large extent, it was my fault because I willingly prioritized career over love. I had a full time job and spent my weekends writing my book, which made socializing more difficult, although I admit now that I’ve used my career as an excuse to stay single and not put myself out there. “I’m too busy to date, I swear!” Yeah right. Everybody’s got time to fall in love.

So the big question is, right now in your life, are you more of a “love” person, or a “career” person? Here’s a test to figure out the answer — visualize your life in five years and focus on which scenario would make you happiest: working a great job, making amazing money but being single, OR working at a possibly-less-great job, but being in love and married? (You can have love AND career, FYI. I’m just saying this because at this particular juncture in your life, you need to choose between the two. Unless the dream job has an office in your current city. Who knows, maybe they’d open one! Sometimes there’s a hidden third option.)

There’s no right or wrong answer here. You’re not a heartless asshole if you say, “I think I choose work!” I personally put a lot of stock into what I do, and I value having a career, but I also know that my job can’t give me blowjobs or take care of me when I’m sick or make me laugh even when I’m wretchedly cranky.

No matter what you decide to do, know that you’re not sealing your fate. You WILL have an opportunity to have your dream job again. You WILL fall in love (or remain in love). Nothing is permanent — life is a continuous stream of fluctuations. Some of them will be smooth and gradual, others will feel like boulders smushing your sense of What You Thought You Wanted. Right now, it’s just about figuring out what slice of your life-pie you can live without for the coming months: the life slice, or the work slice?

Check back each Thursday for Ryan’s latest Call Your Boyfriend column. And you KNOW you have questions — send them to Ryan.