Dear Dategirl,
I have been friends with “Bill” for many years and we’ve shared some kisses. But it never went further, mainly because we both had other involvements. In fact, we both still do have other involvements—for the past few years we have both retained exes in friends-with-benefits-type relationships. This is a situation I would like to end.
I never thought I would fall for Bill, but when we finally had sex last weekend, I was blown away. It was fantastic, and several times he expressed how he wants to see me all the time and has never had such a great sexual connection, etc.
When we parted, I was on cloud nine. I guess I don’t have to tell you what happened next, but I will: nothing.
He wrote a polite e-mail and a couple of semi-flirty texts, but he never once called or asked to see me again. At the very least I expect to be called after sex, so I found this insulting . . . and heartbreaking, really.
I am very sure I want to see him again, but I don’t know if it’ll work out if I’m the one to make the move. So that is what I am asking: Is there any way a woman can pursue a man and still win his heart?
—Old-Fashioned Loose Woman
Didn’t you ever hear that old proverb: “You can lead a man to vagina, but you can’t force him to stick around the next morning?”
There are plenty of ways to successfully pursue a man and win his heart, except that this particular guy has known you for years, finally gave up the ween, and then promptly fled the premises. I know it’s disorienting and utterly humiliating to walk away from an evening of what you considered mind-blowing sex only to discover that the other person came away with the exact opposite impression, but it sounds like that happened.
Or maybe he likes banging you, but doesn’t want to date you. It happens. So he decided to be chickenshit about the whole thing and weasel his way out of being called a fuck-and-dumper on a technicality (i.e., the lame post-coital texts). But regardless of his why’s, the fact remains that you had sex with him, and instead of staying for breakfast, he skittered home and went into hiding. Move on, because it sure sounds like he has.
Dear Dategirl,
My spouse of nearly 14 years and I have decided to divorce once we clear all our debt (approximately $26,000). Do you think it’s OK to seek out those who would be willing and able to have sex with someone who is married?
—Tired of Jacking Off
If you and your wife of nearly 14 years can come up with an agreement to clear your debt and then divorce, surely you can work out a don’t ask/don’t tell policy when it comes to screwing around. However, it sounds like you’ve so far managed to do the nearly impossible and come up with an amicable divorce agreement, so perhaps instead of looking around for tail, maybe you should both devote all your spare time to making more money so you can dissolve this partnership as quickly as humanly possible.
I’m not suggesting this from some moral pulpit; I just know that the longer you linger, the better the chances that it’ll get ugly. Even if you’re both completely over each other, seeing your wife walk in with a hickey won’t be pleasant. Nor will she be pleased to note lipstick smears all over your boxers. You’re only human.
I get that you want to get laid, but if you’ve waited this long, what’s another few months? If it’s completely unbearable, consider hiring a pro, so there aren’t any entanglements.
