Virgin Boyfriend wants to Sleep Around

Warning: Parameter 2 to wp_hide_post_Public::query_posts_join() expected to be a reference, value given in /home/dearhoop/public_html/wp-includes/class-wp-hook.php on line 286

Submit your questions for Dear Hoopers here 

Dear Hoopers,
My boyfriend of 3 and a half years just told me that I took his virginity when he was 23 years old. So, he’s now thinking about sleeping with other women since he missed out. Isn’t this worse than being cheated on? Because now I sincerely have to consider letting him sleep with someone else or it could happen without me knowing. Please give any advice you can think of. It is greatly appreciated!
-Virgin Boyfriend Wants to Sleep Around

Dear Sleep Around,
He’s thinking of sleeping with other women? Does he realize that this could end your relationship? You are clearly not comfortable with this. If you worry he many cheat on you if you do not give him permission to sleep with other people, then you should truly consider the kind of standards you are setting.

If someone wants to be with you they will regardless of the sexual experiences prior to your relationship. It seems crazy to me that he thinks he may be granted a season of promiscuity and you will just magically welcome him back. You do not need to consider letting him sleep with other people, at least not while he is in a relationship with you.

If he wants a hall pass, he needs to be single.


If he’s looking to get a few more notches on his belt, then he’s choosing the importance of sexual exploration over a relationship with you. Sex is an important part of a healthy relationship but it’s one factor of many. If he’s ready to move on then let him go. If he wants a hall pass, he needs to be single.

Dear Sleep Around,
Your boyfriend of 3 and a half years comes to you and tells you that he wants to sleep with other women. Anyway that you look at it, this sounds like a blatant effort at infidelity. I suppose that you could give him credit for being so forthcoming about his intentions, but this is a terrible sign for your relationship. I don’t think this is quite equal to cheating, since it doesn’t appear that he has acted on it and is asking your permission. I would prefer an honest and painful conversation, over someone acting heinously behind my back. However, the implications are nauseating and appear to forecast the end of your relationship.

Technically, it isn’t cheating if you give him permission to do so; this would be considered a sexually open relationship. But as you discussed in your question, your boyfriend’s request puts you in a terrible position to decide the fate of your boyfriend’s sexual fidelity. That isn’t fair to you. You do however have some decisions to make. Decisions about your relationship and your body, that no one can make except for you.

The fact that he lost his virginity with you was his decision and one that he should appreciate, not criticize.

-Dr. Ryan

Lastly, he did give you a reason for wanting to cheat. His reasoning was that you were the first person to bestow your body to him in intimacy. This is not something to be held against you. You gave him a gift and he is contemptuously punishing you for it. Whatever happened in his life before you met him is completely out of your control. The fact that he lost his virginity with you was his decision and one that he should appreciate, not criticize.
-Dr. Ryan