The Candy-Coated Misery of Dating Middle-Aged Bachelors

Even though I’m blissfully, disgustingly happy with Frenchy, who still has that “new boyfriend smell” at not quite four months, I want to share one of the important lessons I’ve learned over the many months I went on a shitload of dates. I have, in fact, assembled a “Do-Not-Date” list for myself that serves as a warning about certain types of ultimately undateable guys. At the top of my list are the guys who have hit 40 and have never been married.

I’m not talking about the middle-aged guys with the big obvious flaws that would render them automatically undateable (e.g. raging alcoholics, drug/gambling/porn addicts, pedophiles and/or Rush Limbaugh fans). I’m referring to the middle-aged guys who seem to have so many good qualities, yet oddly, have never been married. These are the guys who often seem to be too good to be true, the kind who elicit questions like, “Why hasn’t some lucky woman snatched him up yet?” They are snatch-resistant, which is not -- despite how it sounds-- a crude double entendre referring to the dozen middle-aged gay guys in America who are still huddled in the closet. Let me be clear. I’m talking about the kind of guy with a lot of good things going on who has never settled down with a woman, even though he is very much attracted to women. How does *that* happen?

Many middle-aged bachelors claim to want to get married, but complain that they just haven’t had any luck meeting “the right one.” But the problem is, there *isn’t* a “right one.” She doesn’t exist, because deep down, the perennial bachelor really doesn’t want to be married. The idea of being in such a close relationship makes him deeply uncomfortable. I finally gave up on middle-aged bachelors after dating at least three guys like this and being endlessly frustrated by their hot-and-cold behavior toward me. Carny was the worst, as I’ve documented ad nauseum.

I believe this is why things didn’t work out with Penpal and Easy To Talk To as well, although I had the good sense to bail before I spent too much time dating them, or, to put it more accurately, banging my head against the wall trying to figure out what the hell was going on. It sucks when you realize that this great guy you’ve started dating doesn’t want to get close to you. And I don’t mean the great guy you like who doesn’t like you back. Even I’m not egotistical enough to think every guy would want to date me. I realize I’m an acquired taste – like brussels sprouts or Louis C.K.

I’m talking about the great guy who takes you on an amazing date and clicks with you and the whole thing seems to go remarkably well. You both laugh a lot and the conversation flows naturally without too many awkward pauses. You have such a great time that the date goes on and on, until you realize you’ve spend the past six hours together, even though it feels like it just started. The next day or two, you’re so excited about what’s next. Until you realize he’s not contacting you. He seems to disappear for a while. You start second-guessing yourself. ‘I thought he had a great time too. Was I just projecting my own enthusiasm onto him?’ you wonder. He is non-committal about your next date, perhaps claiming to be really busy for the next week or two. 

The truth is he really did have a great time on your date. But instead of getting closer to you, he withdraws, because it’s just too uncomfortable for him to get close to someone. Even someone as fantastic as you. And don’t fool yourself. Even though he’s attracted to you, he’s not going to ignore his deep feelings of discomfort that an intimate relationship stirs up in him. He can’t. Allowing himself to get close to someone is as counter-intuitive to him as running into a building that’s on fire. Or the idea of eating raw fish to the unfortunate, deprived soul who’s never had his taste buds turned on by sushi before.  

He’s had many dates over the years with women as lovely and amazing as you. Why wouldn’t he have found one awesome enough to want to marry? Because deep down he just doesn’t *want* to be married. It’s that simple. And kind of tragic really, because many of them (and there are women like this too) would be such good boyfriends or spouses, if they could somehow get past their feelings of discomfort and panic precipitated by a budding serious romance. I concede it’s possible that there are a handful of unmarried middle-aged guys in existence who really have had bad dating luck, but don’t bet that you’re attracted to one of them. The middle-aged bachelor who is truly open to being in a close relationship, but is a victim of bad dating circumstance, is as rare as the 22-year-old bombshell who falls in love with the rich old geezer for his personality, not his fat wallet. Sure, it’s *possible.* Just not bloody likely.

Date the guy who has proven he can be in the kind of close relationship that marriage entails. Those guys aren’t hot and cold. They’re either hot for you or not. You won’t waste a lot of time trying to decipher the confusing mixed signals that the middle-aged bachelor is so adept at sending. You’ll save yourself the heartache and frustration of trying to get close to someone who is uncomfortable being in an intimate relationship. Would you choose to go to a dentist who is grossed out by teeth? Would you pick a nanny who hates children to care for your kid? If you’re dating to find someone with whom to build a serious relationship, don’t date the guy who *can’t* be in a serious relationship. To steal a phrase from wise philosopher Carrie Underwood, “He’s candy-coated misery.”