Her boyfriend is upset that she wasn’t a virgin when they met. (She took his virginity) He feels like he missed out on exploring before getting into a serious relationship with her. Now she’s wondering how she can make him feel better. Should she give him a free pass?
Hi Bert Show!
I’m in a bit of a kerfuffle and in need of advice. Please bear with me as this might be a long story. I have a boyfriend of 2 years now. He came from a very conservative and religious background to the point that he was not allowed to date while in school and having pre-marital “piano playing” was taboo. That’s actually one of the reasons why he moved to my city because it allowed him to be free and far from his closed minded family. We met in a dating app and everything was great. During one of our first dates he
mentioned that he never really had a serious relationship. For me it was not really a red flag given his history. I was also open to him that I had been in a few serious and not so serious relationships. We really didn’t talk so much about that since he said that’s all in the past. Then after that we started to be more intimate, and that’s when it really dawned on me that I was his first ‘experience’ at 26 years old. It was awkward at first but practice makes perfect.
Fast forward to last week, he was planning something for my birthday and asked me if I have been to this really nice hotel that he wanted us to stay at. I answered yes. I went there with my friend 2 years ago. That’s actually where my friend met her now fiancé. Then he remembered the story I told him that the first night my friend and her fiancé met, they slept together. So he asked me, “So you stayed with them that night?” I was caught off guard. The truth was I was being a good wing woman to my friend so I hung out with her fiancé’s buddy that night so they could be alone. I didn’t want to lie to my boyfriend so I told him yes, but I was in a different room. So he asked if I was with someone then. I just said yes, but it was so obvious that it meant I hooked up with that guy. He was upset about this, especially that it happened just a month before we met.
Somehow he never realized that I have been with other people that way. I think in his mind he was my ‘first’ too. That opened the discussion that it was unfair that I already had all the fun in my early 20s and that he really missed out on this. That he might never get to have experiences too with other people since he is in a very serious relationship with me.
So my question is, is it really unfair for him? What can we do about this? It’s not really his fault that he missed out. I don’t want him to cheat later on in life just to satisfy his curiosity on how it is to be with another woman. Should I give him a free pass? For me, I’m really happy with what we have, and I’m already done with the dating scene. I just don’t want him coming back to me a few years down the road asking for a free pass when we’re married like the other listener you had last week. Please HELP!!!