Friends and Lovers
What to Do
Sweetie girl, you haven't done anything that the rest of us haven't done, or desperately wanted to do, when our hearts have been broken. Sometimes we're so angry and defiant that we'd sleep with someone--anyone--else rather than let that goddamn rat fucking bastard be the last one to touch us. That's "fuck you" sex. Other times it's more of an impulse to overwrite, so to speak, a feeling that if we can just smudge the heartbreaker's fingerprints with a new set, it won't hurt so much. That's "cover up" sex. And sometimes it's just responding to a very natural gratification at being found desirable by someone else. That's "yeah-I-still-got-it-even-if-he-doesn't-want-it" sex. Regardless of the motivation, however, it's usually such indifferent sex that it hardly counts, which isn't surprising considering it isn't really the sex we want, it's just the having done it that matters.
When your boyfriend walked, he relinquished all claims to you. Therefore, you had every right to do whatever (or whomever) you wanted, wherever, whenever, etc. So, no, it wasn't cheating. But I wouldn't tell him; I'd slip this into the what-he-doesn't-know-won't-hurt-him file and forget all about it.
I find your resolutions to problems to be very realistic and accurate. With that said, I will start with the cliché that I have never written to an advice columnist before but am curious to see what you have to say about my small dilemma. I like my best friend's sister and would like to ask her out, but I am ambivalent about putting our friendship at risk. While he likes and respects me, I am also his "bar partner" and we have met a fair amount of women when we go out. He knows I like to date and do quite often. He also knows I am a gentleman and that I treat women nicely, but he may not be happy with me going out with his sister. I like her, but I don't know her well enough to decide if asking my friend for permission is worth endangering our friendship. Any advice?
Well, aren't you a doll, buttering me up like that; I feel just like a Thomas' English muffin. And in return, let me say you have a lovely way with a euphemism. Because, unless I'm reading you wrong, what you're really saying is that you and your friend count on each other for support and encouragement when it comes to trolling the bars for sex. It doesn't matter that you treat these women well. Few guys--even the ones willing to consider any woman perched on a bar stool fair game--want their own sisters involved with a fellow who "dates" a lot. Especially since your interest in her is admittedly casual.
To try to understand this more clearly, imagine your mother was single and dating. Would you want her to go out with a guy you'd seen picking up women in bars--someone you were pretty sure was looking for nothing more than a brief encounter? Of course it would be her business, but it's the unusual son whose protective instincts would not be aroused. It's the same with brothers. As long as you're still casually dating women (plural), and not looking for a woman (singular) for a potentially serious relationship, I'd leave this guy's sister alone--at least in any romantic sense. If and when the time should come that you are thinking about an exclusive relationship, and if at that time you find yourself strongly attracted to her, then it might be different. In that case, out of respect for your friendship, you might want to alert your buddy to the fact that you wish to court his sister, but the only one with the right to give you permission to date her is the lady herself.
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