Any advice for a 32 year old virgin?

Dear Ms. HeartBeat:
I really hope you can help me with my problem. I am a 32 year old virgin, who has never dated for various reasons. The chief reasons are because I have suffered from depression, painful shyness, social anxiety, and an overall low self image.

Over the past few years, I’ve managed to work through many of my issues and put other aspects of my life (financial and professional) in good order. I feel like I’m finally in a position to at least start dating. I’ve been comfortably attending social functions (mostly Meet Ups), but I’m still too shy to approach men.

I don’t know how to flirt and I have difficulty picking up on signals that men may be interested in me. I’ve misread kindness as interest on two different occasions. Basically, the guys were friendly and seemed to like talking to me. Later, I found out that both guys had girlfriends.

Even if I ever get a date, I fear that my complete inexperience will scare away the guy. How do I tell if a man is interested in me? How do I tell a guy that I’ve never had a date, or do I even reveal this information?

I’d eventually like to have a sex life, so when or should I ever tell a guy I’m dating that I’m a virgin? I’d really appreciate any advice on my predicament.

Signed,
Tired of Being a Virgin

Dear Tired:
Let me begin by saying how proud I am that you took the bull by the horns and did something about your problems. Most people wallow in self-pity; whining forever about what they don’t have, don’t know how to do, etc. It’s very refreshing to get a letter where the person writing admits they have issues, and tells me what they’ve done to overcome them.

Meet Ups are a great way to socialize with people of sexes, forming friendships and getting comfortable interacting with strangers. Meet Ups remove a lot of the unknowns because each one is targeted to a specific audience, all there because of a common interest or goal. Good job with that too!

There are a couple of guidelines that you should follow that might help you get over the hump and handle your first dates with aplomb:

Every man that you talk to is not trying to date you. Some guys just want to interact with you on a friendly, social level. Do not assume that because a man approaches and strikes up a conversation that he wants a relationship or even a date.
Don’t worry about approaching men for dates. What you do in social settings is make yourself approachable. For most men that means a woman that looks pleasant and happy… that smiles. If you go to a Meet Up by yourself and talking to a guy sitting next to or near you makes sense, then strike up a conversation. Talking about the lecture you just heard, the book discussed, making a comment about something someone near you said, etc. are all great icebreakers.
A date is not a relationship. Even five or ten dates are not a relationship. The purpose of a date is to spend time with someone getting to know them, and letting them get to know you. That’s it! So unless you two sit down and talk about what you want to see happen in the future and agree to be a committed couple, he is not your boyfriend. That means you are free to go out with and talk to as many other men as you like. Remember that.
Flirting is light and fun – not a sexual invitation. For more information on how to flirt (and how not to), read my article on flirting for women here.
Never tell a man that you haven’t been on a date. Your past is none of his business really. What you can do is tell him that you’re “out of practice” or “really rusty” which is true but doesn’t make you sound like a complete novice. He’ll feel that your awkwardness is cute and do his best to make you feel at ease. Such a revelation will bring out the Knight in most men.
Not every man you go out with needs to know that you are a virgin. Only the man that you decide you want to sleep with needs to know all that. There are many, many men that seek out women that have little to no sexual experience with other men. To such a man you would be highly desirable. As you get closer with a man and feel that you want to experience sex with him, that’s when you would let him know that you haven’t had sex before and you hope the experience with him is as memorable as you’d dreamed it would be. He’ll take it from there.

Finally, there is no need to tell them about your struggles to arrive at where you are – that sort of revelation should be shared with only the most trusted man that you are in a serious long-term relationship with. Casual dates do not need to have all that personal data on you. Just tell them about where you are and the wonderful person you are right NOW.

Good luck!!

MsHeartBeat

Relationship and dating advice columnist of Ask HeartBeat! Has enjoyed dishing out insightful yet hilariously funny advice, tersely worded reality checks and "let me slap you upside the head" wake up calls to men and women around the globe since 1991.