Over 40, Gay and Single: Entering Back Into the Dating Pool At MidLife

Navigating the dating world is difficult at any age.  When you no longer have youth on your side it can seem like and even more daunting task to date, especially if you've been out of the game and in a relationship.  As someone recently out of a three relationship with someone 6 years younger than me, one of my biggest concerns in the beginning (vain as it may have been) was that if we were to break up he'd still be sitting pretty in his youth and I'd be approaching the hill. 

When our relationship did end and I finally decided I was ready to date again I realized I was a bit out of touch.  Being over the bar scene and having never really gotten into apps or online dating I felt lost.

It’s true that age is irrelevant when it comes to some standard-issue dating challenges, such as how to compete on a crowded playing field or, more specifically, find someone who matches your commitment level.

But, in other ways, dating in your 40s is a whole new ballgame. Hurdles don’t disappear; they just change. To get past them, maybe you need to get a new game plan.  Here are some common issues and solutions to dating over 40.

You're rigid and set in your ways

One advantage of age is self-awareness—when you know yourself better, you don’t waste as much time on bad dates.  Johnathan, 42, says, “I am more careful about first dates and dismiss pointless second dates. I  can recognize dysfunction faster now than I did when I was younger.” That’s smart time-management. But, if you aren’t careful, a too-stringent approach can prevent you from being open to love when it presents itself.

Ask your closest friends for regular feedback to make sure you aren’t becoming too stuck in your ways. Singles in their forties often experience “burned-finger-on-stove syndrome.” After touching the flame a few times, you learn that love can hurt. But as Kevin says, “I realize that love doesn’t happen when you’re overly guarded. Sometimes, when I’m concerned that I’m being too quick to judge, I check in with close friends.” Singles who don’t have (or don’t invite) intimate feedback from either a partner or close friends miss out on the emotional mirror that helps us grow and escape bad patterns.

Also, challenge yourself to try something new dating-wise every week or two: Try a new place to meet and mingle; chat with someone who isn’t your “type” and otherwise stretch your boundaries. You might be surprised at the positive changes that can bring.


When you’re younger, dating relationships face challenges related to coming out, such as building self-esteem and rising above homophobia—but it’s easy to meet prospects. In your forties, after years of working on yourself, you’re once again struggling to gain self-esteem. The hurdle this time? Let’s get real: Ageism exists in the gay community. Self-esteem is the rock that every aging gay Sisyphus pushes up the hill yet again. “When I turned 40, someone gave me one of those over-the-hill cards and I was pissed off and a little depressed,” says Kelvin, 46. “My friend meant it as a joke, but that card made me confront my a fear I didn't really know existed: Was I really over the hill?”

Confront your fears about aging head-on rather than buying into them. As Men Po, relationship specialist, notes that “In the gay community, negative stereotypes reinforce the belief that gay relationships are based solely on physical attraction, and that once youth starts to fade, we are unlikely to have any real or lasting relationships.” Avoid the trap by treating age as a number, not a mental prison sentence. Jason Jackson, 49 is a good example of someone who, changed his mindset and opened up to new ways of thinking.  "I stopped the internal criticism. Now, I focus on what I can improve, not on the number. I’m happier in my own skin.” It’s important to focus on being your best at every age, as well as the ageless characteristics (i.e., loyalty, humor, strength) you want in a great date.

Eligible Men

What happens when the Olympic-sized dating pool you’re used to swimming in suddenly seems like a lap lane? “The dating pool gets smaller within people your own age because most available guys are partnered, or there are good reasons why they’re single,” says Kelvin. In addition, the bar scene also starts to lose its allure with age, maturity and career demands.

Hop on the Internet and cast a wider net. That’s what Daniel did. “Staying at home got boring after three months,” he admits. “I accepted that bars and clubs didn’t work for me anymore. Online dating was a more comfortable way to meet guys closer to my age and have fun.” Thankfully, the stigma of dating online is gone. As Malcom, 45, of Virginia, notes, “To meet other guys, gay men in their forties are going online. The Internet is bringing new hope to those of us who don’t have a ton of time or want to hang out at bars.” It works, too—he met his current partner via online dating.

Other positive ways to get out of the dating dugout and onto the playing field include volunteering and immersion in social and athletic activities. Follow the example of Stephen, 43, of Brooklyn. “I got out there and got involved in my interests—I took a course in art conservation and actually began going to gallery openings rather than throwing the invitations away. I was pursuing what I loved—and met some great dates, too.”


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