My [25 F] friend [28 M] of about five years, asked me if I'd have sex with him because he's a virgin and 'I have a lot of casual sex anyway'. I feel insulted and, more importantly, sad and horrible about myself. Is it fair to be angry with him, or am I projecting anger onto him/not being rational?

TLDR: My friend asked me to have casual sex with him, because he knows that I've had a lot of casual sex, so that he can learn how to have sex/not be a virgin anymore, and this question made me feel angry with him and terrible about myself. I don't know if I should be angry with him, or if my anger is fuelled by a general lack of self-esteem and being mad at him would be unfair.

Hey,

Background: This shouldn't be too long, but I should briefly run through some background stuff for this situation to make any sense. I've only had one proper relationship, from age 17-20, and he left to study in another city on a scholarship. It's been five years, but it still saddens me to think about, and I suppose I've struggled to commit since. For the past five years, I've just been having one-night stands and short, unemotional flings. I should also state that I was diagnosed with bipolar roughly 6 years ago, although I'm only 'moderate' on the spectrum I'm far more likely to engage in casual sex in manic periods. Recently, I've been feeling down in general, and very down about myself and my appearance. In the past month, I've decided that I no longer want to have casual sex. I've met a number of guys since making this choice, and instead of going home with them I've exchanged phone numbers instead, and said that I'd like to hang out again. I've not heard back from any of them, and I know my down-swing isn't helping anything, but it's been reinforcing this idea that I'm only good for a quick fuck, not good enough to pursue, not 'partner' material.

So anyway, I invited some friends to a gig on the weekend, one of these friends being 'Ben'. Ben and I have been relatively close friends for the past 5 years, not one of my closest friends, but quite close. He's a very anxious person, he has a hard time in social situations- ordinarily he's very polite, almost to the extent that his politeness becomes frustrating. I told everyone that I was going to have a cigarette outside before the band started, and he said he'd come out with me to have a chat. Outside, he says 'so this might be a weird question, but since you've had a lot of casual sex and I'm still a virgin, would you have sex with me, to just like, show me the ropes?' I was mildly shocked, so I just said 'I don't think that that'd be healthy for our friendship' and we didn't talk about it again. But it upset me a lot, and days after, I still feel upset about it.

Ben and I have never been at all flirtatious, we've always been 100% platonic- we don't even hug as a greeting/a way to say goodbye like I might with other male friends. I thought the proposition was insulting, because, it just cements the idea that my sexual worth is of an unemotional, casual nature. When he asked his tone was like, I don't know, asking a friend to help you move your stuff from one house to the next, or for a ride to the airport. To be fair, I'm honest with my friends about my sexual history, and I will joke and tell stories about one-night stands that were amusing... I understand why he would think that I do have a casual attitude towards sex... but was this question reasonable, or am I right to feel objectified in a sense?

Basically, I don't know if my poor self-esteem reinforced by a month of failed attempts to actually date is the reason why I'm angry at him (making it displaced anger, which would be unfair to him), or my anger in feeling insulted by him and this proposition is justified? I feel like I need some unbiased advice. Since I have bipolar, I try extremely, extremely hard to employ self-awareness so as to not subject anybody to emotions or reactions that aren't fair or justified, but in the same way I fear that I let too many things slide in fear of this happening.

Submitted September 21, 2019 at 11:07PM by whatodough38 https://ift.tt/330WF90