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Ask Dave-Feeling too old to date? Look online!


One midlife man despairs that he’s seen and done it all and become jaded towards love. Dave helps him lighten the burden of his psychological baggage.

By Dave Singleton

ear Dave,
I am turning 49 next week. The idea of going on a date with a guy seems so impossible to me right now. I have had many relationships, some lasting several years, and now I am looking at being 50 and single, and the thought terrifies me! I feel like I have dated too much, know too much, expect so little, and that I stopped believing in love a while ago. But I can’t imagine life single forever. Any advice?
– Older and Still Single

Dear O&SS,
There’s an adage I’ve seen displayed on t-shirts and pillows that reads, “Getting older ain’t for
Quality also means that you are putting energy into your dates.
sissies.” Many gay men would agree that this bumper-sticker wisdom applies to dating at midlife. But no one is saying you shouldn’t date! So let’s take on your concerns one by one.

You’ve dated too much?
Since the Internet made coffee dates and hookups as easy as logging into your computer, it’s a challenge to remember that quality counts. Quality doesn’t just mean that your date is attractive, successful and shares your interests. Quality also means that you are putting energy into your dates, making sure that you are available and willing to focus on the people you meet.

You know too much?
One positive about getting older is that, hopefully, you know more about yourself and what you want. There’s no closing the door to what you’ve learned. But somehow, you have to stay smart and open. The combination of the two is true wisdom.

You expect so little?
Sometimes, older gay men have a hard time transitioning from youthful dating expectations. Perhaps you’ve been “once burned” and are now “twice shy,” as the saying goes. But the reality is that if you stay shy and don’t risk, you won’t get anything. Maybe the people you meet will have a little bit of baggage. But don’t we all have some by our 40s? Yes, it’s true that you don’t look or feel 25 anymore. So why put unrealistic expectations on you or your date?

You stopped believing in love?
Really? Would you be writing me if you’d totally closed down shop? Maybe it’s that you stopped believing in the kind of naïve love that you can only trust when you’re young. The good news is that there’s a deeper, more mature love that allows for the wide spectrum of experience and truth. But as gay men in a youth-obsessed culture, you have to be a willing romantic pioneer to attempt that journey.

When you’ve been around the block a few times and are still looking, I know it’s not easy. Dating in your 40s and beyond is challenging (and I speak from experience). Why? For every 20-something entering a first dating relationship full
Avoid the trap of chasing the elusive gay fountain of youth.
of wide-eyed wonder, there’s a 40-something back on the market after another relationship ends. One is learning the rules; the other has “been there, dated that” and wonders, “Now what?”

Given that dating at midlife is a whole new ball game, see if these tips help you develop a game plan that’ll make turning 50 a little less daunting:

Work with your new reality.
You might not want from a partner what you wanted 20 years ago. You might appreciate ageless characteristics, such as shared interests and values more than you did when your sole dating criteria was, “Is he hot?” It might be comforting to stop chasing younger guys and find a partner your age who can relate to your experiences and your outlook.

Treat age as a number, not a mental prison sentence.
Avoid the trap of chasing the elusive gay fountain of youth. Just because gay culture tries to convince you that shirtless, late-night clubbing with 20-somethings is what really matters, you don’t have to buy into it. Instead, focus on your worth at every age, as well as the ageless characteristics (i.e., loyalty, humor, strength) you want in a great date.

Choose your venues wisely.
For many gays at midlife, bars and clubs don’t work as well anymore. They lose their allure with age, maturity and career demands. Smaller parties, events focused on hobbies and avocations, volunteering and online dating can be more comfortable ways to meet guys closer to your age. Yes, it’s true that the Olympic- sized pool of dating prospects you swam in years ago suddenly seems like a lap lane when you reach your 40s. So the best bet is to cast a wider net and diversify.

Be self-aware, not rigid.
One advantage of age is self-awareness. The pro is that when you know yourself better, you don’t waste as much time on bad dates. Dating may seem faster. For example, you are more careful about first dates and quickly nix pointless second dates. You assess fast if he wants the same level of relationship as you, whether that’s casual or committed. You recognize dysfunction and mismatches faster now than you did when you were younger. All of these are smart time-management tools. But avoid becoming overly rigid. Ask your closest friends for regular feedback (yes, ask them to give you input on your actions and choices) so you don’t get stuck in your ways.

Finally, despite the fact that there’s not enough discourse in our culture about gay men in midlife, remember that you aren’t alone. Many gay men are in the same boat as you, and it’s easy to see why. We haven’t had many role models for finding significant and satisfying relationships as we age. My hope for you, and for all single gay men at midlife who want to date, is that we’ll confront myths and fears about aging now so that we don’t have to buy into them later.


Dave Singleton, an award-winning writer and columnist for Match.com since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at davesingleton.writer@gmail.com.
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