I am a 23-year-old straight male. My ex-girlfriend and I started dating in high school, when we were both 17, and continued dating until I broke up with her the summer after our freshman year in college because things felt too serious. We continued to have sex, but I blocked out all my feelings for her, while she was open about still wanting to be with me. She started dating someone else sophomore year. I realized then that I still wanted to be with her, and I broke down emotionally and made both our lives difficult while she was dating this new guy. I was a very unattractive person then. I also found out other details by snooping. I know that during the time we dated, she faked orgasms with me. She didn’t have one with me until she introduced a vibrator the year I was having emotionless sex with her after the breakup. This made me feel inadequate. Since then, we have forgiven each other and tried several times to rekindle our romantic relationship. Unfortunately, while for me there is a sexual attraction, she says she is no longer attracted to me. I’m sensitive, fashionable, and artistic, and she tells me she’s more attracted to the “all-American-man” type. She is currently dating someone long-distance, and they have been together for seven months. But we still talk about “us,” we still cuddle, and she’ll say things like “When I think of growing old, I imagine doing so with you.” She views our intimacy as “friendly,” while I view it as more romantic. I try to be a good friend, but hearing emotional crap about her relationship makes me want to scream, “WTF are you doing? No guy will ever clear your bar, because I set the bar!” Do you think there is any chance that we will be together again? Am I nuts to still want this girl? —Her Ideal Mate
There are six other continents on this planet—six in addition to the one your ex-girlfriend currently resides on—and my advice for you, HIM, is to pick any other continent and move there. Get. The. Fuck. Away. From. Her. Not because your ex is evil, HIM, but because this relationship is over. She’s not only seeing someone else, she’s made it clear that you’re not her type. She’s not into sensitive, fashionable, and artistic types—she may not be into entitled assholes, either—and it’s time to take the hint that she’s practically pegging you with. And I gotta say…
This relationship is never going to be what it was, because neither of you is ever going to be what you were—that is, you’re never going to be 17 and in love for the very first time again. The bar you’re talking about, HIM? Hormones set it, you didn’t.
Also: It sounds like you behaved terribly after you dumped your ex. When you wrote, “I made both our lives difficult,” I read, “I stalked my ex.” (Snooping after a breakup? That’s a stalker move.) And having “emotionless sex” with someone who has “blocked out all [his] feelings” for you—being treated like a Fleshlight by someone you still have feelings for—is rarely a pleasant experience, HIM, and it must’ve been particularly painful for your ex back when she still wanted to get back together with your arty-farty ass.
So perhaps she’s treating you this way—keeping you on call for cuddles, dropping hints about getting back together (in old age!), dumping “emotional crap” on you about her current boyfriend—in a subconscious effort to get revenge. You tormented her then; she’s tormenting you now.
But whatever her deal is, the bottom line is this: When two people aren’t good to each other, when they’re not good for each other, they should get the fuck away from each other. —Dan
My husband and I are both in our mid-20s. He’s in the military, and our relationship, though imperfect, is strong; we’re both happy with—and good to—each other. Not long ago, we decided that a “monogamish” arrangement appealed to us both, and we renegotiated the terms of our relationship. He recently got orders for a yearlong deployment, and one of the many things we need to do before he leaves, I think, is have another conversation about nonmonogamy. I think we should adopt a “don’t ask, don’t tell” policy. I doubt I could tolerate the inevitable stress of this upcoming year if I were expected to abstain from sex for the duration. But it’s unlikely that either of us would want to hear about the other’s casual hookups when we’re separated by nine time zones. Yet I can’t bring myself to speak up, because I’m already so jealous of the people he might fuck while I’m on the opposite side of the world and unable to fuck him myself. Suddenly, the thought of my husband with someone else is nearly intolerable. What would you do in this situation? —Worried I Fear Estrangement
If my husband were about to deploy to a war zone, I would probably do what you’re doing, WIFE: I would worry about sex—I would worry about the people who might want to fuck my deployed husband—because that would provoke less anxiety than worrying about the people who might want to harm my deployed husband.
Talk to your husband, WIFE, and put that “don’t ask, don’t tell” policy on the table. Considering that you’ll most likely have more opportunities than he will over the next 12 months, a DADT policy may be precisely what your husband wants while he’s deployed. And share your feelings of jealousy with him. Those feelings are not only normal and natural, WIFE, they’re a good sign. It would be more worrisome if you didn’t care who he fucked and he didn’t care who you fucked. And your husband may share your chief concern: It’s one thing to think about your partner fucking someone else when you’re around (and you’re able to fuck your partner, too, and remind your partner why he’s with you), and it’s quite another thing to think about your partner fucking someone else when you’re not around.
Feelings of jealousy and insecurity can make a person feel like she’s not cut out for a monogamish relationship. But it’s working through those inevitable feelings of jealousy and insecurity—with your partner, not your sex-advice columnist—that proves you are cut out for one. Good luck, WIFE, and I hope your husband comes home safe and sound. —Dan
If you have two friends, one male and one female, who are both married (not to each other) and looking for an affair, is it okay to put them in touch with each other? May I bring them together in the same way I would two single people—throw a party with lots of alcohol? The man is in a sexless marriage and wants to get laid. The woman is getting divorced and needs to get laid. Note: The man and I have sex every few months. It’s awesome sex, and he has a gorgeous body. I would like to offer this to my female friend, who could use it, but I’m not sure how he would feel about being passed around. What should I do? —Is This How Ashley Madison Got Started?
You should go the liquor store. —Dan
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