Dear Bossip: I’m A 29-Year Old Virgin & I’ve Been Dating For 5 Months, But I Haven’t Told Him Yet

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Categories: Dear Bossip, Love and Relationships, News, Sex and Relationships

Black woman in bed

Dear Bossip,

I have been dating this great guy for about 5 months now.

We have known each other for a little over a year because we work together. He is such a patient man, but at the end of the day he is still a man. We have not been having sex yet and I am getting more and more concerned that he is going to want to know why a 29-year old woman is holding off for so long, or he ends up cheating because we are not having sex. So, I have decided that I am just going to do it already. But, my question is should I tell him before we have sex that I am a virgin or just get it over with without him ever knowing? Please help. – Virgin In Waiting

Dear Ms. Virgin In Waiting,

Uhm, hmmm, so you’re a 29-year old virgin, and you’re dating this patient guy, but you haven’t told him yet that you are a virgin. And, you figure you should just lay with him, and give up the goods because it’s been five months and you think he may be wondering why you’re holding off. And, on top of that, you’re asking if you should or should not tell him you’re a virgin, and just do it without telling him and he won’t figure out that you’re a virgin. Bwahahahahahaha! Girl, I can’t!

You think he won’t notice when you get in the bed, and he’s inserting himself that he won’t figure out that you’re a virgin? SMDH! I think it will become apparent to him for a number of reasons, particularly by the way you move, and how you respond to him. But, I don’t suggest that you do this. Please don’t give yourself to a man you’re not certain about, and especially because you don’t want to lose him. Sex doesn’t keep a man. Trust me when I tell you this. Don’t ever use sex as a bargaining tool, ever!

But, let me get a few things straightened out with you. I applaud you for being a 29-year old virgin. That is commendable. I hope it’s because you’re waiting on the right guy, and that you have some morals and standards.

But, herein lies the problem. You say he is a patient man, but, is he a good guy? Is he the man you plan on seeing yourself with for the next year, five years, or ten years? If you don’t see yourself with him for the long haul, then do not just have sex with him because you’re afraid of losing him. Ma’am, that is so damn childish and immature. If his only concern is when he is going to bang, or get you in the bed, then it’s not worth your time or his. Get out of the relationship. If you’ve waited this long, you can wait a little while longer.

And, let me hip you to something, there is a difference between a good man and a patient man. Some men will wait you out, while at the same time pressuring you for sex. And, a good man will wait until you’re ready, and won’t pressure you into doing something you’re not ready to do. So, if you’re considering giving up your virginity just to appease his sexual appetite without regard for yourself and your morals and values, then no, do not engage in sex with him until you’re ready to do so. Don’t jeopardize your body just because you think or feel he is going to wonder why a 29-year old woman is holding off from sex. That is silly and juvenile. Girl, stop this!

Please note that although you’ve known him a little over a year, you’ve only been dating him for five months. I suggest that you have a heart-to-heart conversation with him about you being a virgin. Let him know why you’ve been maintaining your virginity, and how much it means to you to be with the right guy, and not compromise yourself just for the sake of having a man. If you’re waiting until you get married, then you need to express this to him. Be honest, and truthful. Having this conversation will hopefully allow the both of you the opportunity to explore your relationship, and where you see it going.

Also, if it’s been five months and he hasn’t brought up trying to get in your pants, then it says something about his character. He may be a stand up guy, but, again, I do urge you to have a conversation with him about your virginity. He may be willing to wait, and not be concerned or bothered by it. And, I want you to be clear that you are the one who is feeling pressured or uncertain about your relationship because you feel it’s been five month without sex. And, you FEEL and THINK because he’s a man he may get tired of waiting, and may cheat. If this is how you FEEL and THINK, then your relationship is not solid and he hasn’t made you feel confident in the relationship and where it stands. Or, you’re bringing some past issues into your relationship. Either way, you need to have the conversation with him and find out how important sex is to him, and in the relationship.

And, I have a big policy against dating someone you work with. Honey, do not –ish where you work. It’s not good. What happens when the relationship ends and you’re working together, and have to see one another each day? Ill feelings may be present, and you may not be ready or emotionally and mentally well to see him day in and day out. You start bad mouthing one another, saying nasty things, and doing things to sabotage them at work. And, that’s just the tip of the iceberg. Dating someone in the workplace is never a good idea. NEVER!

So, ma’am, you’re in a double jeopardy. You’re dating someone you work with, and you’re a virgin who is considering giving up your virginity to him because you’re uncertain about the time he’s waited, and if he will step out because you’re not doing it. Yeah, I think there are some insecurities underlying in this situation. Perhaps the best thing is for you to be honest with him, and tell him you’re going to hold off on the sex. At the same time, you need to work on you and making sure you feel comfortable in a relationship with a man where sex is not the determining factor. Best to you! – Terrance Dean

Hey Bossip Fam, what do you think? Share your opinions and thoughts below!

Also, e-mail all your questions Terrance Dean: loveandrelationships@bossip.com

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author terrance dean

Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15); Hiding In Hip Hop (Atria Books – June 2008); and Straight From Your Gay Best Friend – The Straight Up Truth About Relationships, Love, And Having A Fabulous Life (Agate/Bolden Books – November 2010; $15). They are available in bookstores everywhere, and on Amazon, click HERE!
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