This is a bit of a long, fucked-up story.

I've been having an affair with a older married woman with three kids for the past 10+ years. She claims her husband doesn't know about us, that she doesn't have sex with him anymore, and that she sleeps in a separate room. She requires me to be monogamous to her and, hence, doesn't allow me to date anyone else. You might wonder why on earth I put up with this, but we get along amazingly well. She's witty, funny, clever, intelligent, and drop-dead sexy. She's the best friend I've ever had. Every time we're together—if I'm not depressed—the conversation just flows. Plus the sex is pretty great, although she's not as kinky as I am and is a bit reluctant to do stuff I would like to do. Finally, and maybe most importantly, we've both made sacrifices to be together: I've turned down jobs that would require me to move overseas, and she's completely changed her career to be with me. So, in many senses, it's much more like a real relationship rather than an affair. It's just we can't easily go on holidays together, we rarely spend the night together, and we don't often get to spend the evenings together.

Why am I writing? Because I feel like my life is slipping by, and I'm not entirely happy. I don't like being alone in the evenings. To cope with the situation, I drink too much in the evenings. It's hard for me to have friends, as by nature I like to be friends with women, but the woman I'm seeing gets insanely jealous and assumes I'm trying to fuck them. I'm 38 and would like to be married. I don't have any kids, and I'm not sure I actually want kids, but I would like the option of having kids. (I'm an only child, and it would make my parents so happy if I did have kids; they occasionally drop the passive-aggressive comment about me being the "end of the line.") The married woman I'm seeing did get pregnant by me, twice, and decided to have abortions both times, rather than actually open up a conversation with me about whether we should start a full and proper life together and raise a family. She's past childbearing age now so there's no chance any longer of us having kids together.

The rest of the letter... and my response... after the jump.

Setting aside the issue of kids, I would also just like to be able to go on a holiday with someone without having to engage in the cloak-and-dagger planning rituals. I would like to host dinner parties with friends—you know, all the stuff that normal couples do. Why don't I leave? See earlier remark about her being the best friend I've ever had. I can't imagine a life without her. Besides, I've tried to leave her several times in the past for other people, but have never been able to do it. No one compares to her.

This is where things get interesting. About a month ago, a 27-year-old woman made a pass at me. I was at a low point, and so I decided to follow it up and see where it went. We started emailing, texting, then sexting, then had sex. This new person is like a sexual godsend for me. She's willing to do absolutely anything (bondage, watersports, anal play, and she says she would happily have threesomes and group sex), and she calls herself my "sex slave." She has also said she wants to have kids at some point in the future and, since she's really into me, she said she would like to have kids with me. From the very beginning, I was honest and open with her about the married woman I was seeing—which was hard for her to take, but I told her that I couldn't walk away from a 10+ year relationship for a relatively unknown stranger. So she's reluctantly agreed to put up with the situation for a little while until we get to know each other better. She the first person I've met in 10 years that I can actually imagine leaving the married woman for.

But this is the problem: I can't really talk to the 27-year old. There's a small language barrier (English isn't her native language) but, really, it's that she's not talkative, she doesn't ask questions, and she doesn't seem to want to talk about the news, or books, or films. She says she's not this way with other people, but that, for some reason, it's hard for her to talk to me. I suspect she could be good to talk to, as she's funny and chatty over text, but in person it's just weird, awkward silences a lot of the time. Furthermore, the age gap, while great from a kink perspective, is just enough that it makes cultural references hard to share.

So, that's the problem. On one hand, I've got the perfect intellectual match who—if I could marry—I would love to spend the rest of my life with. But she won't leave her husband to be with me. (Trust me, I've asked her many times. She's made and broken so many promises to leave I can't count them anymore.) On the other hand, I've got the perfect sexual match who I probably could marry and have kids with and a normal life with, but whom I can't really talk to, and whom being with requires giving up my best friend.

Not sure what advice you might have (see a shrink?), but I'd love to hear it.

The Middle Ages

Blah blah blah. Your problem is a lot simpler than the length of your email would seem to indicate.

You face a choice, TMA—and it's not a choice between a woman with whom you can talk who has a husband and kids at home, control issues, a jealous streak, and a limited sexual repertoire and a woman who is good at texting and fucking but not so good at talking. It's a choice between the women you're with currently—and the dead-end relationship your in currently—and 3.5 billion other women on the planet you could be with.

And that 27-year-old woman you've been seeing for a month—one lousy month—is just one of the 3.5 billion other women on the planet.

The more time you spend with the 27-year-old you've been seeing for a month, TMA, the more shared experiences you'll have, the more you'll have to talk about. She could wind up being your chatty wife, the fecund mother of many, many children (presumably yours), and your sex slave and piss buddy and anal queen for life. Or not. You might just spend a few great months with her, have tons of amazing sex, and wind up single and alone again/for the first time in a long time if/when this relationship implodes. (And my money is on "when," TMA, as the odds of implosion are always higher when two people start talking about kids and marriage after a month.) But "single and alone again" doesn't necessarily mean "single and alone forever." If things don't work out with the 27 year old, TMA, there are still 3,499,999,999 other women on the planet.

Finally, TMA, if the married woman you're with now—the married woman you're with now—is as invested in monogamy (cough, cough) as you claim she is, TMA, it's impossible to read the affair you're having (not to be confused with the affair she's having) as anything other than your hand slamming down on the eject button. You want out and—consciously or subconsciously—and you're engineering an out. But waiting for Ms. Ten Years to find out about Ms. Four Weeks is the cowardly way to go about it. Ova and up and end it honestly.