Dear Michael:

I read you all the time in Gay San Diego and I usually like what you have to say, so I decided to ask you the question that, after much soul-searching, I cannot answer: why am I still alone? I am a 44-year-old gay man, nice-looking, smart, successful…all that stuff. Most of my friends have found partners in recent years, but not me. I’m not sure what I’m doing wrong. In fact, I think I have more to offer than some of my friends, but they are the ones who end up with great guys and I don’t. What am I doing wrong?

Tired of being Alone


Dear Mr. Tired:

You ask a very valid and complex question. Without knowing you, I will do my best to answer. Here are some possibilities to consider:

Sometimes we are so defended that we (subconsciously) prefer to be alone rather than risk being hurt. Someone once hurt us and we are terrified to be vulnerable again. Is this you?

Many of us compare and judge what others have and think it looks good, but we can never know what any one else’s relationship is really like. It may look good on the outside, but is very unhappy on the inside.

Are your expectations too high? Do you meet many men who are interesting to you? When you do, what happens? Do you indicate interest in them or do you expect them to do all the work, read your mind, overcome their own insecurities and jump through all your hoops?

The author Roxane Gay recently said, when asked about love: “Some people never find the one, or there are several people for whom you have such feelings or you think you have found the one and they change or you change in ways you can no longer tolerate. Love is so damn messy.”

I agree. Finding a good partner is probably one of the most complex tasks in life: much harder than finding a good job or a great place to live. Two people, bringing all that they’re proud or and ashamed of, coming together and working through all the uncomfortableness that dating and falling in love brings…that’s not easy, for anyone.

If you were my client, I’d ask you: “How kindly do you treat yourself, now, as a single person?” This is a good reflection of what you can expect in a partner. If you are kind, forgiving and loving to yourself, you can expect the same from a potential boyfriend. If you have ultra-high expectations for yourself and punish yourself when you don’t meet them, guess what? That’s the kind of lover you’ll attract.

And, honestly, why be miserable until you meet Mister Right? Does your life have to be on hold until he shows up?

Have you ever noticed what sorts of people are considered attractive? It’s not all about looks, clothes or fancy cars – although, that’s definitely a bonus. Attractive people are happy, confident and enjoy their own company. And happy, confident people attract other happy, confident people.

I’m not encouraging you to fake it; I am encouraging you to find ways to enjoy your life nowand not wait until you have a great partner to be happy.  Do you have good friends, people you love and can count on, or are your friendships superficial? Good friends make life so much better, especially if you’re single. And go for depth: it’s easy to have surface-level friends, where you don’t talk about anything meaningful (like your unhappiness with being alone). Real friendships have the capacity to include conversations about the stuff in life that scares/upsets us.

If you have these kinds of friends, talk with them about your longing for a partner. If you don’t, begin to cultivate people you feel safe to really open up to.

Over the years, I’ve been single and coupled – many times – there are pros and cons to each. I respect your desire for a great partner and strongly encourage you to begin to treat yourself the way you want your future partner to treat you: ironically, this will only help to bring someone wonderful into your life…and sooner.