To settle or not to settle? Gay/bi man on dating women. Help!


Dear Megan,

I’m not able to find much of this on the internet as most searches direct me to gay men married to women who don’t know their husbands are gay, and my question is about gay/bi men who ultimately decide to date women again.  So hopefully you can help.

I’m gay. I find women attractive, and enjoy sex with them, but my preference is for men by far. I would like to find a man to share my life with, but since starting to come out a few years ago I’ve had a difficult time finding a guy that knocks me off my feet. I have a female friend – she’s a coworker, close friend, and we actually briefly dated- who knows I’m gay. She’s been trying to date and is having a horrible time meeting the right guy, as well. We’re both in our 30s. We’re both looking, unsuccessfully.

We’re both lonely. We share a lot of values and goals. We have a lot in common as far as friends, lifestyle, and coworkers go. But I don’t know what kind of passionate sex would be there… Would it be crazy to entertain dating her if I’m honest with her?

I acknowledge that this could be playing with fire. I’m more curious if this is a pattern that others have observed. Lonely gay man and lonely straight female find love and companionship in each other. I don’t want to call it a marriage of convenience, but after a long conversation with her today about our trials and tribulations with dating, it crossed my mind and got me wondering…  Thoughts?

-Don’t Call Me Will Truman


Dear “Don’t Call Me Will Truman,”

Wowzers.  It’s not every day I get to introduce a gay man to WAG (“Will & Grace”), but I can assure you that if you binge watch the 1998-2006 revolutionary hit sitcom this weekend you’ll have your answer…  But perhaps you want a more personal response than a lazy “Now, remember kids, what did TV teach you?” one, so here it goes.

According to you, you’d like to find a man to share your life with but can’t seem to meet a wolf that knocks you off your feet.  In comes your female coworker friend.  You get along well… you’re both in the same boat… you have similar values, goals, friends, lifestyles, etc… and now it’s got you thinking, “Maybe we should just be together…”

No, you’re not crazy to entertain the thought.  For, gay or straight, your logic has taken you to the same place everyone who gets tired of dating ends up, and it’s called the land of settling…  To settle or not to settle, that, indeed, is the question.

Interestingly, the answer to your question of settling is two-fold.  When it comes to whether or not you should pursue your female coworker friend, the answer is no.  Why?  Because you declared that you want to share your life with a man.  Period.  End of story.  Thanks for coming.  It’s been fun.  (Hey, don’t get mad at me that you let a clear desire slip from your pen and I refused to overlook it in your state of confusion…  But alright, you got me. There’s more.  After all, I did say the answer was two-fold…)

However, you are right in letting this female friend run interference in your love life.  You see, not only have you given yourself an awesome partner to help combat your loneliness and do “couple stuff” with while you wait for Mr. Right, but you’ve allowed yourself to see that you’re capable and ready to be more open in your dating criteria and, well, let’s just say, “adjust” your standards.  With that knowledge, you can then extend the criteria you used to consider settling down with this female coworker to men instead of limiting Mr. Right to someone who knocks you off your feet.

When you focus on cultivating more friendships, like the one you’ve developed with your coworker, with men, you’ll increase your chances of meeting like-minded souls with similar values, goals, friends, lifestyles, etc., who also fit your desire to share your life with a man.  And, don’t worry, you don’t have to give up your desire to be with someone who knocks you off of your feet, just know that “knocked off your feet” moments don’t always come in the beginning.  Sometimes they come after you’ve already started to get to know someone, and sometimes they even take a couple years!  Hence the surprise.

So, do follow the criteria you have with your coworker and “settle” for a deeper connection with the man you see yourself sharing your life with when you close your eyes.  And don’t let dating fatigue discourage you from starting fresh, staying open, and enjoying the harmonious relationships you’ve cultivated in your life thus far…  At least until you’re 87.  Settle all you want then.  Best of luck.

-Megan 🙂

For my story check out “The Care and Feeding of Sex Symbols” here

To submit your question to “Dear Megan” click here!

“Dear Megan” Home Page

To Subscribe to my YouTube channel click here!

Note: As this column is designed to be a judgement-free zone, only those who have been, (or know someone who has been), in a similar situation are invited to comment; especially if the question is unorthodox or hard for one to relate to.  And for even more relevant insight, those seeking answers are always encouraged to go within.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s