Q I'm a straight guy, married for 16 years, kids in school. My wife cannot find a way to be intimate with me. We've had therapy individually and together. I nearly divorced her, but we decided to stay together—we do love each other, and the economics and child-rearing favour it. After I asked for a divorce, she fucked the shit out of me for the first time in 10 years. That was the last time she fucked me. When the subject of affairs came up in the past, she said, "I wouldn't blame you." I could jack off only so many times before I cracked. I went online and met a very sexual woman with a strictly NSA thing for married men, and we fucked. I plan on doing it again. I know this could go all kinds of bad ways, but divorce just isn't realistic. I don't want to head into my 50s with 10-plus years of celibacy behind me and decades of celibacy ahead of me. But I want to keep my marriage. Which kind of idiot am I? —Help Understanding Boundary-Breaking Yearnings
A If I were required to answer particular types of questions based on the percentage of the mail they constitute, I would answer two questions like yours every week, HUBBY. The majority of the mail I receive is from unhappy people in sexless marriages they either don't want to end (they have kids, they do love each other, everything besides the sex is working) or can't afford to end (they don't have enough money for lawyers or two households, one depends on the other for income/health insurance/caregiving).
So which kind of idiot are you? The most common kind, I'm afraid.
I'm going to take a break from questions like these—from questions like yours, HUBBY—because I'm sick of the subject and my regular readers must be, too. But for you, HUBBY, and one last time, here's my advice for people in your situation: Do what you gotta do to stay married and stay sane. Have a convo with the wife about the accommodation you require to stay in the marriage. Reassure her that you're prepared to spend the rest of your life with her while emphasizing that you refuse to be celibate for the rest of your life. So every now and then, for your own sanity, and for the greater good, you're going to have sex with other women. If this isn't something your wife can accept, HUBBY, then your only other option is divorce.
Q These are things I (28, gay, male, single) did last night, and they show how fucked up I am. 1. I hooked up with a guy off Craigslist. It was lame, he wasn't cute, I was bored. 2. I came home and went on Tinder (which says I'm looking for an LTR, despite that hookup). I saw a guy from the gym—but he didn't swipe right, and I was devastated. 3. I went online and sold a pair of my used undies. I don't know what I'm doing with my life. I could use some advice. I'm sure what you say won't be nearly as bad as what the voice inside my head is yelling at me. —What Is My Life?
A 1. I hooked up with this dude once, and it happened so fast—and it was so sleazy—that I had to fish his driver's license out of his wallet when he was in the shower because I couldn't remember his name. And that sleazy hookup led to a relationship so good that I wound up marrying sleazy hookup dude. So in my experience, WIML, and the experiences of millions of other people in LTRs with people they fucked the first time they met, hooking up isn't proof that someone isn't looking for an LTR. So that underwhelming hookup doesn't make you a hypocrite, okay?
2. Gym dude isn't into you—just like you weren't into the dude you hooked up with last night. Are you into every dude you see at your gym? No. Do you swipe right on every dude you see on Tinder? No. So last night you got rejected quickly and impersonally—but you've dished out that kind of rejection too. Don't be a hypocritical baby about it, okay?
3. You made an underpants perv very happy, WIML, and you made yourself a little money. Nobody was lied to or misled, no one got hurt, and the total amount of joy in the world ticked up slightly.
One eventful night does not an out-of-control sleazebag make. But if you feel out of control, WIML, take things slower. Resolve to be a bit choosier about who you hook up with, remind yourself to be grown-up about rejection when it comes your way and refrain from kink-shaming yourself the next time you make an underpants perv's day.
Q I've come into professional contact with a respected and successful artist. She is a woman in her 60s; I am a man in my 40s. I'm really attracted to women who are strong, talented, and smart. She's all that, and funny. I've never been attracted to someone that much older than myself. Nobody bats an eye when a guy gets with a woman who is 20 years younger, but how do I pursue her without her thinking I have some creepy fetish? Am I a creep? I don't think so. I've gone out of my way to make her feel special on several occasions, but it has only caused her to remark on my great customer service—and not in a flirty way. How can I let her know that I want to move into something else besides a professional relationship without creeping her out? —She Makes A Real Turn-on
A Set aside the age difference, and how you met, and those sexist and dehumanizing double standards. (An older man with a younger woman is an attractive guy with game, an older woman with a younger man is a fetish object with no self-respect.) Set all that aside, SMART, and what do we have left? Person A is attracted to Person B; Person A doesn't know how Person B feels, so Person A has to hit on Person B. Even if Person A does their best to mitigate the risks of creeping out Person B—Person A is polite, respectful, and does their hitting on by "asking out" not by "lunging at"—the risk cannot be entirely eliminated.
Your best bet, SMART, is to be unambiguously direct with her ("I think you're great, and I'd love to take you out on a date") and to invite her to be unambiguously direct with you ("If you're not interested, just say no—I'm a grown-up and I can handle rejection.").