Dear Richard: The Bitter Truth About Dating

By: Dear Dick

Dear Dick,

I am recently out of a 16 year relationship. I met my my ex-spouse when I was 25 and at 41 suddenly found myself, (pardon the pun) thrust into singledom. I was not only shocked, but frankly disgusted at the attitude of the gay men in the community when it comes to relationships. What happened to the guys while I was living my life in the suburbs? 

I have never heard as much BS shoveled as guys that supposedly want to date. Some of my favorites to date:

• "Date?  Oh no, we cannot go on a date, we can be friends and see where it goes".
• Him:  "I want to get to know you better..."   Me:  "Like a date?" (refer to comment above)
• Said by a 50+ year old to me...  "I don't see myself settling down until I am in my 60's"  (good luck finding a nurse maid. I will change a partners diaper if we built a life together, but not yours because you decided you don't want to die alone)
• Him:  "I see myself having a boyfriend and I spend 2-3 nights a week at his house and him 2-3 at mine".  (Seems an awful lot like dating to me).
• Well, I see my partner having a drawer at my house and me at his, that way a split is easier.  (Nice, start a life together with the exit strategy already in place).

I have talked to friends about this and the only thing I can seem to come up with is that suddenly the word "date" doesn't mean to "get to know someone", it is like you are engaged and picking out china patterns. Am I reading this wrong?   

It also appears to me that gay men want some sort of guarantees that life is going to be rainbows, unicorns, and flying monkeys shooting out of your ass 24 hours a day, seven days a week, as there can be no drama.  Do you have to be Rebbecca of Sunnybrook Farm all day every day, and never have ups and downs?  

I can tell you after 16 years that life is messy. We had divorces of family members, deaths of grandmothers and parents, changes in employment status, etc.  So, to add the remark, "Oh, and no drama", I am guessing that I am the only person on the planet not to have grown up at Disney's Fantasyland. I am utterly confused.

I get the feeling that gay men seem to be of the opinion that if you are friends with someone first, it is automatically going to work out. The problem, I have never slept with a friend, nor do I plan to as that is the surest way to lose a friend. I have always found that after I get to know someone so well, I know way more about that person than a boyfriend should know, and I don't ever want to sleep with them (That orgy on top of the post office in West Hollywood, where you got fisted with no lube...yikes!).

How is a single man supposed to find love in a community that wants marriage and yet has no respect for it at the same time? I am tired of people wanting to find out what is behind the next zipper, and not actually wanting to get to know the person to which that appendage your after is attached. Have I become too unrealistic or jaded? I am beginning to feel that I will spend the rest of my life alone.


Jaded in Love, or Too Idealistic


Dear Jaded,

Wow. Pretty angry. The intensity of your frustration makes me wonder the circumstances of the end of your 16 year relationship. Are you getting back into the dating pool before you have finished with the huge life changes that must entail? Regardless of the reasons for the end of the relationship, it is a huge adjustment.

The experience of dating after being in a long-term relationship can be challenging. But just as you say, life is messy. That includes the baggage that most men carry about seeking companionship, so you might as well add that to your list of the dramas that come with a fully-lived adult life.

You have been in the demilitarized zone for 16 years and the shock of being in the trenches of dating ambiguity must be like being dropped on a battlefield. The good news is that you know what it's like to be settled in with a companion. That is very different than dinner and a movie with a virtual stranger. Add sexual attraction on top of that and it's a pretty volatile mix. But knowing what the pleasures of a companionable life are may be the vision you need to keep in the back of your mind to help you be a bit more compassionate about the vagaries of your prospective dates.

Another question though, when you say "the gay men in the community" what community are you talking about? Bars and clubs? We have found there is no one gay community. There are various communities that may offer a better assortment of dating choices. Have you tried gay men's hiking, biking, running, clubs for example? Many large cities have them. Also, there are gay service groups that focus on fundraising and community volunteering. The great thing about them is that even if you don't meet anyone you'd like to get more cozy with, you got some exercise and did some volunteer work for those in need.

So, what if all the (long) list above of your beefs with the dating pool is true? Then what? Giving up the goal of companionship doesn't seem like a great idea. The only thing you have control over here is your own point of view. If you really want to mate, you may need to work with the realities here. Developing patience and compassion for the dating pool may seem like a tall order, but if you have been in a long-term relationship, you know that those aspects of your personality will be constantly in use. Think of it as training for the big event! We wish you the best.


Dear Richard is not a medical doctor, a licensed psychiatrist, a counselor, a reverend, or a rabbi. He has not been evaluated by the FDA, the CDC, or the BBC, and his words are not intended to diagnose or treat any condition. The information is for educational purposes only and it not intended to serve as medical advice. Dear Richard does, however, love hearing from you and answering your questions. Leave a comment or send him an e-mail.