Crazy Good Advice

posted by Steve Bortstein - 

Dear Steve,

First, I hate that I’m writing to you about this. I’m a loyal listener, but I listen to you because you make me laugh and you make it easier for me to hate the Cowboys. I didn’t want to write to you when you started this silly bit, but here I am.

I started dating a really wonderful man about a two months ago. He’s extremely smart, good-natured, funny and all that jazz. I’m extremely happy to have met him, and even happier that he likes me as much as I like him. But before he came along, I hadn’t had a serious relationship in some time. Needless to say, I’d gotten quite comfortable with the single life – doing what I want, when I want, how I want.

Now, I’m quickly remembering what it means to be in a relationship and realizing relationships are much different at my age, 35, than when I was younger.

My man has this bad habit of mentioning past sexual experiences. I’ve never had to deal with this because all the men before hadn’t been that experienced, so they didn’t have much of a sexual past to share. That’s not the case here.

He does not go into detail (thank God) and I don’t think he realizes his stories bother me. I think he genuinely trusts me, and simply wants to talk about these things because he’s never talked to anyone about them before. I want him to be open and honest with me, but part of me feels like, when it comes to his past sexual experiences, I just don’t want to know.

I’m sick with jealousy and with insecurity. Sick with fear that I don’t really know him. I’m not worried that he’s going to cheat on me, but that maybe I won’t be enough.

So now I’m turning this over to you, the last person I should be talking to about these things, since you’re kind of bad at this sort of thing as you’ve mentioned in the past.

So go ahead and tell me what to do.

Signed,
I’m Already Regretting This

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