Miss Information: I’m overweight, shy, and insecure. How can I lose my virginity?

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Miss Information

Have a question? Email Letters may be edited for length, content, and clarity. 

Dear Miss Information,

Breaking up is difficult, especially when you were never a couple. We met at school. We were both twenty-one and single. I started falling in love with her, and then she started dating a thirty-three-year old. I told her about my feelings and she was amazing about it, even though she said she wasn't sexually attracted to me and couldn't see us as a couple. 
We had amazing dates and loved holding hands and being arm-in-arm. It might not have been right, but I enjoyed every single moment. Her boyfriend rarely did anything with her, so I may have simply been filling a void.

I eventually found out that she was going to break up with him because he wanted to have sex and she didn't. At first I was relieved and excited, but I quickly became scared and started imagining the worst. She's slender. He's a former weightlifter. She wants to break up. He doesn't. She's alone at his place. Arguments escalating to violence. She winds up hurt. And so on. 
I tried calling her cell the day she was going to break up with him but couldn't reach her, so I called her house, and her older brother picked up. They don't get along very well, so he only knew that she'd left work and nothing about what she had planned for later. He invited me out for coffee and took a liking to me, which made me want to be with her even more. He felt his sister was being used and that the boyfriend was no good, and that it was time for him to step in. Awesome! 
Not awesome. I received a call after getting home. She found out what I told her brother and was angry, which I understood since what she told me was private. However, I put her safety over any sort of intimate relationship I'd been longing for.

I've tried calling her a few times since and even bought her flowers but no luck. It's been two months and her birthday is coming up. I plan to call her to wish her a happy birthday but I'm not sure what that would mean. I do, however, know that the call will be the extent of it.

I'm still wondering though if I should have said anything to her brother, if I did good by putting her well-being above my desires, and if I should wish her a happy birthday. — Alive and Well

Dear Alive and Well, 

There's a thin line between concerned friend and stalker-in-training. Perhaps "stalker" is a harsh word. Why don't we go with "unintentionally selfish and overbearing?" It's the only phrase I can think of to describe a lovesick schlemiel who goes out for lattes with his non-girlfriend's estranged brother, shares secrets that weren't meant to be shared, and leverages a fantasy about dating violence to position himself as the Superman to his crush's Lois. 

You do want to be Superman, Alive and Well, however much you may be in denial. The history between you two may be twisted, but it's very clear that you adore this woman so much so that you're willing to look beyond all the negatives. (Like her not liking you. Aaaaaand her already having a boyfriend.)

You've managed to convince yourself that you're being some kind of altruistic super friend, but it's my duty as an advice-giver to tell you that you're not. The day-of-the-breakup worrying, the meeting with the brother, the birthday call all of those are attempts to deepen your relationship with her. You say you'll ring her up, say happy b-day, then leave it alone. I don't think so. Because I've been there. We've all been there. You want her to interpret it as a touching gesture, a welcome relief from the searing loneliness of having all her friends ditch her on her special day. Maybe she'll ask if you're free that evening. Maybe you'll wind up having coffee and pie with a candle in it at a cozy little diner. Then, she'll lock herself out and have to spend the night at your place. Without pajamas. 

Not going to happen, Alive and Well. Vigilance and (arguably) good deeds alone will not make someone love you. Moreover, if you genuinely believed her safety was in question during this breakup business, offering her an escort to his house and/or giving a vague heads-up to a neutral friend should have been the start and end of it. The rest is up to her. As far as the phone call, do the best thing for her well-being (and yours) and drop it. She knows how where you are if she wants to find you. 

Dear Miss Information,

I'm a twenty-year-old straight male virgin with very little experience with women. Actually, make that no experience. Generally, I've either been rejected or haven't even taken the chance. I have always had pretty crappy self-esteem. I'm not that attractive, not very tall, pretty overweight, and slowly becoming more introverted and insular.  

Whenever I talk to people about my lack of a sex life, I get told, essentially, "Just wait. It will happen," and, "You don't need to rush it." I feel that these are some of the biggest lies ever told. Maybe I'm being a little paranoid. I know there isn't some conspiracy to make me stay a virgin forever. But I don't think my friends really "get" my anxiety about sex and sexual relationships; beyond the physical pleasure, it's important to me to have someone value my body and share hers, and make a connection.  

Am I wrong in that belief, especially since I have never been close to the real experience? If that's the case, would changing my outlook really transform me and help me meet women? Should I be annoyed with my friends, or are they speaking some truth? — Right or Wrong

Dear Right or Wrong,

Your friends are right and wrong. (Don't worry, this gets more helpful.) They're right in the way that inspirational photo plaques in your nana's bathroom are right. "Good things come to those who wait." (Imagine a hungry tomcat peering into a fishbowl.)

They're wrong in the sense that there are some steps you can take to help your virgin era come to a close. You need to create a social life and emotional foundation that are conducive to losing your virginity. Getting out of the house more often will help, as will cultivating relationships with female friends and getting in the habit of talking to strangers (especially female strangers), even if it's something as stupid as asking for directions you don't need. The journey of a thousand penises starts with a single smile. Other steps include taking better care of yourself and losing weight if you need to, as well as visiting a shrink and signing up for an online dating site.  

I know what you're thinking with that last one. Oh sweet Christ, the rejection. Yes, there will be rejection. But guess what? It's happened to every single non-virgin out there. I don't care if you've already tried a few and failed. Try again. You want to join the club? You gotta pay the price.

You ask if you're wrong in the belief that sex is about connection and the meaningful sharing of bodies. I'd say you're right. Sometimes. Other times it's a drug, an escape, an experiment, a psychological weapon, or simply mindless fun. When your friends take a blasé attitude towards your concerns, this is them trying to tell you that your first-time expectations may be a little unrealistic. It takes multiple partners and perspective to come to this realization, and I don't blame you for not being there. I wouldn't be either. What you need to do right now is realize that you have value, my good sir, whether or not you've found someone to value your body through the act of intercourse. 

Readers, any other recommendations for Right or Wrong? Are there any special tricks to succeeding at online dating if you're lacking in the looks and experience departments?