Ask Amy: Single man seeks dating advice

Dear Amy: I am a 58-year-old gay man and have identified as bi for most of my adulthood. I have had significant relationships with both women and men.

After my last relationship, more than 15 years ago, I became unavailable and essentially asexual, barring a few random hookups with men. I’m now feeling like I would like another significant relationship, but I feel like it needs to be with a man.

The “problem” is that I do not come across as gay. Women hit on me all the time, but men seem to not realize I’m available or possibly interested. As a contributing handicap, I am not attracted to most gay men.

How do I go about meeting potential mates without surprising, angering or terrifying the guys I’m attracted to?

Amy says: Like you, in middle age I was single for more than 15 years, “barring a few random hookups with men.” (And like you, I might have terrified a few men along the way.)

However, you are not responsible for another person’s “terror” at your interest or availability.

Because you are interested in pursuing a serious relationship with a man, you should do your best to get involved with organizations where you are likely to meet other gay men. Also, ask the next woman who hits on you if she knows any great guys who might be interested.

The online matching experience can be a mixed bag, but this is an efficient learning experience for anyone looking to meet new people. You should do some online and in-person research to see if this appeals to you.

Dear Amy: I have a “newer” friend. Let’s call him “Timothy.” We have been intimate a few times. Timothy has made it very clear that he’s open and willing to do it again, anytime I want.

During our last visit, Timothy talked about how attractive the women are at his workplace. He said he’s unsure if he could successfully compete with other men to ask them out.

This rubs me the wrong way, but I’m unsure how to talk to him about it. Even though we are not “officially” together, I don’t feel comfortable that he is telling me that he wants other women, while also wanting me.

Am I overreacting? Any suggestions would be appreciated.

“I am willing to do it again anytime you want” conveys a willingness to have sex with you again if you’re into it and your schedules align. While Timothy might believe that this is a generous statement, it is expressed with the same personal connection a person might have toward scheduling their next dental appointment.

He has implied that he doesn’t have a chance with the attractive women at the office — but that’s where you come in. I believe you might have misread Timothy’s intent regarding you. You have already had sex; now it’s time to try to have an honest conversation.

You should ask him, quite simply: “Are you interested in having anything more than a sexual relationship with me?” After that, no matter how he answers, if you want to form a personal and exclusive relationship with a man, you probably should keep looking — because this guy sounds like a jerk.