Mailbag: Being the single guy

by GK on October 15, 2012 · 5 comments

Our mailbag question comes to us from my friend B in Philly. Some context first: His close friend SW from Philly recently got into a relationship, which SW chronicled in his guest post on dating women who are busy.

“I’m turning 27 soon, and my friends who are all in the same age group are now more likely than not to have a serious girlfriend, fiancee, or to be married. In a way I knew it would happen, but it’s still strange to see it happen in real life.

Since you’ve met SW, he’s a perfect example. He’s a cool guy (and remains so), but the times of every Friday and Saturday night 9PM pregames, watching Swingers, hitting the bars, and reciting countless stories of what girl X and Y did or didn’t do all seem long gone. Instead, crazy pregames are shifting towards having dinner with other couples, trips to the beach are no longer ‘guys weekends’ … What happens when these friends of yours get married???! AHHHHH!

It would be also super cool to hear how you handle being the “Token Single Guy” as you approach 30 and beyond … my friend and I agreed that most guys in general, regardless of age, tend to settle for a woman who isn’t necessarily what they want, and it seems tough to explain to ‘regular people’ why you haven’t settled down yet once you’re in your late 20s or later.”

In some ways, I’m the wrong person to ask about this. Here in San Francisco, there’s really no such thing as the token single guy. The locals, frustrated by years of online dating, consider this the most commitment-phobic city in America, and with good reason. The latest Census showed that 82 percent of San Franciscans between 25 and 34 had never been married. No major city had a larger percentage.

So if all else fails, B, move to San Francisco! Distract yourself with single friends, yoga, mountain biking, skiing, world-class food and drinks, social media, casual hookups, start-up businesses and endless niche hobbies! That’s what most of us do.

Still, I’ve outgrown that Census stat: I’m 36 and have never married. I also know what you mean. In the last three years, I’ve seen most of my closest male friends and relatives get married or move in with girlfriends — even some fellow ex-Charisma Arts instructors, and we were the very spirit of bachelor adventure while we worked together.

celine dion all by myselfI too wistfully remember pre-gaming with my two regular wingmen and enjoying nights of wanton debauchery — until I was the last single man standing. I’m still friends with all these guys, but there’s no denying that the dynamic changes. And it should change, for the sake of their relationships. When guys like SW are truly happy with their women, I’m happy for them.

Finding other single friends is easy enough if you live in a big city — lots of guys (and girls) in your age range are seeing their friends settle down and are in your boat. You just need to get out of your comfort zone and meet some new people, much like dating again after a breakup. Yeah, it takes a while to create that kind of bond again, but I’ve made it happen.

As for your committed friends, their availability will vary, but until they have kids, some genuinely will want to hang out, even if their girlfriends must come along.

If she’s cool, she might even want to help you mingle. Lucky for me, one of my ex-wingmen is living with his girlfriend, but they happen to be swingers. So if we go to salsa class, we’re all looking to meet people and she has no shame about playing wingwoman.

As for the stigma of being single, just be thankful you’re a guy. The occasional woman will tease me when I tell her about my coaching or blogging, with some quip like “Why are YOU still single then?” But I’ve never heard a guy make such a remark. It’s because we don’t bear a woman’s social or biological burden to couple up, and we’re less likely to see bachelorhood as some kind of Loser Hell — purgatory maybe, but not hell.

As you said, however, there are still plenty of guys who settle. I always think of the poem by Charles Bukowski in the clip below from the documentary about him.


I cover some of this in my Peter Pan post, but anyone with half a cerebral cortex should know that in this age and this economy, marriage and kids can no longer be seen as the finish line to a successful life — even if you’re married with kids. There’s a Grand Canyon-sized gap between committing and committing well. And a man’s longer shelf life, if he takes care of himself, can keep him attractive to relationship-minded women well into his 40s or beyond.

Like you, B, if my life depended on having a serious girlfriend or wife, I’d have one by now. I could have had many, in fact. But chances are I’d probably be divorced or broken up, because I realized sooner or later that she wasn’t right for me in the long run, and I would have had to be someone I wasn’t to stay with her. I’m grateful that in some cases, she realized it first and cut me loose.

Explaining why you’re still single implies that you actually have something to explain. I go to bed every night, usually alone, with a clean conscience, fortunate with my place in the universe. I can’t say the same for those poor saps who sleep every night with a woman they wish they could do better than.


1 SW November 21, 2012 at 8:03 am

Excellent article, GK. I am just now catching up on your posts and saw this mailbag one from B. I like your take on being unapologetic for being single.

I think a guy who is single by choice says a lot about his character. He’s happy in life and not willing to settle for second best – rightfully so. I am in a very happy relationship for this same reason. It is harder to balance my time between friends and my girlfriend, as I’m sure it is for anyone in a good relationship.

But as you pointed out, sometimes I can line them up to have both occur at the same time to satisfy both parties. Although it happens significantly less than before, I also try to hang out with ‘just the guys’, which is something I know we all would like to do every now and then. I can appreciate that.

2 D December 6, 2012 at 4:39 pm

Gk, do you never want to get married? The city I live in is much lonelier if you are alone. Many of my male friends all have to ask for permission to go out… so if your not with somebody, it can feel like solitary confinement.

Girls who even want commitment seem to be way too addicted to “meeting new people” with online dating.

How do you suggest a guy go about “Getting out of his comfort zone?”

3 GK December 6, 2012 at 10:01 pm

These are good questions, D. I never want to get married to the wrong woman. If I meet the right one and I feel my life would be enhanced by making that commitment, I’ll do it. But I don’t feel that I MUST marry in order to be happy.

Even in a smaller city, there’s bound to be another single guy you can hang out with. You just have to find him. As for how to get out of your comfort zone, it depends on what the guy’s comfort zone is. But if he needs to make more friends, he should make that a daily habit, just like taking a shower.

4 D December 8, 2012 at 12:00 pm

Yes making new friends. I get how to meet a girl, at least the concept, and have done that a few times. But all my friends were from school it seems. I was just curious on how a guy can go about making more friends.

5 GK December 8, 2012 at 5:26 pm

You can do what I’ve done to make friends: look out for activity groups that appeal to you, such as improv, running, hiking, etc. Most cities have groups like that.

Otherwise, potential friends are all around you. Go to a bar or coffee shop and just chat someone up. You might be surprised how receptive they are to talking. Then be the guy who organizes outings, and you’ll make even more friends. It’s no different from pickup, really.

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