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Dear Prudence,

I’m a middle-aged gay man. With the exception of a high school girlfriend, with whom I quickly broke up with before I figured out my true identity, I’ve always had relationships with men.

A few months ago, I met a woman and I fear I’ve fallen in love with her. She’s smart, beautiful, and we have many things in common. I thought she was just a good friend but I’ve found myself feeling attracted to her in a way I’ve never felt attracted to a woman. And I think she is attracted to me too. What’s going on here? Maybe I’m bi? That would be insane since I’ve always been proud to be gay! I love men! Although apparently now I also love this woman. Am I just in the midst of a mid-life crisis?

It’s confusing. I don’t know how to explain this to any of my friends for fear they’ll laugh at me, but at the same time I feel she likes me and I like her, so why not give it a try? Then I think about how tackling my first serious relationship with a woman in my forties is crazy. I thought I had this all figured out over 20 years ago. Can you really change your mind about something as big as this?

—Blindsided

Dear Blindsided,

You’d be surprised at how many times I start a response with “We’re all going to die one day. Do what you want!” and then delete it as I try to come up with something more specific to a letter-writer’s situation. This is one of the times that that thought entered my head. My strongest feeling about your dilemma is that mutual attraction and love are hard to find, and if you’re lucky enough to be experiencing these things, it would be a shame to let overthinking what you should be doing (and what people will think about what you’re doing) interfere. Don’t talk and analyze yourself out of happiness.

To take it a step further, I’m guessing that your love for men and your pride in your gay identity has at least something to do with the life-affirming feeling of following your own attraction even when it comes with challenges or isn’t rewarded by society. Well. You may have another chance to do that now.

That said, I don’t want to minimize how destabilizing it must be to contemplate this big shift to your identity and maybe even your whole social world (though, of course, bisexuals are definitely a part of the LGBTQ+ community!). To take it down a notch and make it feel less overwhelming, what if you were to tell yourself a different story about what’s happening? So, instead of “I have to decide if I’m bi!” or “I’m changing my mind” or “I might be in a mid-life crisis,” you might say, “I’m attracted to and interested in a woman and the jury is out on what that means for my future or how I label myself.” After all, it’s only been a few months. And even if your feelings stand the test of time, it’s not as if you have to file official paperwork for a sexual orientation change. No one can stop you from throwing your hands up and saying (to yourself and others) “It’s surprising, isn’t it! Life is crazy. We’ll have to see what happens.” And no one can stop you from still thinking of yourself as a gay man who is having an experience he didn’t expect, while making peace with the fact that in the minds of some people you are now bi.

No one can deny that being gay has been a huge part of your life for decades and has shaped who you are. No one can predict who you’ll be drawn to in the future. And who knows—your transparency about the whole thing might create some openness and understanding in a friend group that doesn’t sound like it’s the most supportive. I was a little bothered by the idea that everyone would laugh at you if you admitted being attracted to a woman, and it suggests to me that there might be others in your circle who are holding things back because they’re afraid of being mocked or shamed. You could set an example that gives others permission to stop hiding the parts of themselves that they worry make them weird or threaten their sense of belonging.

Addendum: After writing all that, I re-read your letter and realized that while you are in love with this woman, you’re not even 100 percent sure if she’s attracted to you or at all interested. If she is, everything I just wrote stands. But I also want to add that when you approach her about your feelings and your desire to date, you should be super clear about your attraction to her but also your ambivalence about what it means for your identity. Falling in love with a man who doesn’t really want to let go of being gay and has a lot of doubts and insecurities about what the relationship means could be pretty tough. And your current mindset means her future with you would be uncertain. You’re on a journey that is 100 percent allowed and nothing to be ashamed of, but she should get to decide whether she wants to go along for the ride.

Dear Prudence,

I have developed a huge crush on my best friend’s husband and I don’t know how to deal with it. I would just try to avoid him, but we have developed a friendship over the years as well. We have a lot in common and get along really well, so it’s just natural that he frequently joins us when I have plans with my friend. She always asks me first, but at this point it would be weird if I started saying no.

I would never dream of acting on these feelings and I don’t think he has any kind of non-platonic feelings towards me whatsoever. I was hoping my crush would go away on its own in time, but it’s only getting stronger because he’s such a great guy. How do I nip this in the bud for good?

—Crushed

Dear Crushed,

Normally I’m pro-crush and anti-crush-shame. That’s because normally the actual feeling of a crush is pretty harmless, even when it won’t or shouldn’t lead to a real relationship. But yours makes me a little more nervous! I think it’s because even if you have absolutely no intention of trying to make anything happen with your friend’s husband, the crush itself feels like a violation of her trust. I know that’s not fair because you can’t help your feelings. And the important thing is that you aren’t going to act on it. I just worry about how she will feel if she gets even the tiniest inkling about what’s going on from the way you involuntarily giggle a certain way or blush when he talks to you. After all, she knows you well and I assume is familiar with what you’re like when you’re infatuated with a guy.

Because of this—and because I want you to avoid anything that could be perceived as flirting—I think you have to stay away from him. And it’s okay to lie a little bit to make that happen. Tell her something like, “You know I love Jake and I generally don’t mind at all when he hangs out with us, but I really need to talk to you privately about something embarrassing /I’ve been feeling down about being single and think it’s better for me not to be around couples for a while /dating has been rough and I want to pretend men don’t exist for a little bit.” Commit to your excuse or excuses for as long as you can, and mix them up with inviting your friends to some activities that naturally exclude her husband—a spa-themed sleepover, bra shopping, whatever. During this time obviously avoid his social media accounts and by all means, never communicate with him one-on-one. This is key. Meaning even if you were thinking about throwing a surprise birthday party for your friend that would require strategizing with him, scrap the plan. Commit to this distance for a few months.

All of these suggestions are meant to create guardrails to prevent your crush from becoming obvious to your friend, to keep it from turning into actual flirting or an emotional affair, and to starve it of new input with the hope that it dies out, like most crushes eventually do. At the same time, you might do some journaling or just thinking about what’s really behind your infatuation. Could it be that this guy is actually a great match for you and you have chemistry with him and would want to date him if you met him in the wild? Maybe. But I’m sure he’s not the only person you know who checks those boxes. So it could be that your feelings are telling you something about yourself.

Jasmonae Joyriel, a licensed clinical psychologist, writes in a blog post on the topic that a crush may highlight “a longing for novelty or spontaneity, a craving to be desired, admired, or seen, a reminder of playfulness or freedom [or] unmet emotional or physical needs.” Maybe thinking of your feelings as primarily being about your personal growth rather than this one specific guy could help. When you approach a crush with curiosity, Joyriel advises, it can act like a mirror, “reflecting your deeper desires … even the ones you haven’t named yet.” And of course, there’s that deep desire that you are already aware of: Keeping your friendship intact. So make sure you spend more time thinking about how great she is and how good that relationship makes you feel than you do thinking about her husband.

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Dear Prudence,

I’m an only child. I had difficulty making friends as a child, as a teen, and as a young adult, and now that I’m in my 70s, I’m STILL having trouble making friends. What do I do now?

—Friendless

Dear Friendless,

I can imagine that having had this struggle for a long time might make you overthink every interaction and potentially get in your own way. Maybe you hold back out of fear or being rejected, or try so hard to connect with people that they end up feeling put off. Or maybe you’re aiming for a version of friendship that the media has convinced you everyone else has, but instead of recreating the Golden Girls, you should just be looking for someone to have coffee with. If you manage your expectations, I believe there is hope, and that success will come from being really transparent and explicit about what you want.

Recently in my local NextDoor community, a woman shared that she was a new mom feeling isolated and was looking for people who would like to join her for walks at a particular park at a particular time of day. The response was overwhelming. I’d suggest you do something similar. You don’t have to say “I’m lonely and need friends,” which I know feels very vulnerable, but you might try “Looking to meet people who will join me for Zumba class at the senior center on Wednesdays / who would like to run errands together on Monday mornings / who are open to getting our dogs together for play dates on Saturdays / who would like to help me make jam with the fruit that grows in my yard.” When these gatherings happen, follow the conventional wisdom about first dates: Don’t talk excessively about yourself. People like it when you ask them a lot of questions. The psychoanalyst and relationship expert Esther Perel advises, “A good question on a date is one that yields a lot of information and stories and associations, without putting people too much on the spot.” If nothing comes up naturally, she says movies always make a good topic.

If possible—and I know this is as tough when you really want friends as it is when you’re searching for love—try your best to focus on having fun in the moment instead of fretting about whether the person likes you back and where the relationship will go.

Classic Prudie

I’m a woman in my 20s living with a roommate. She’s mostly a good roommate, but she doesn’t have many friends, and seems to want me to fix that for her. Whenever I visit a friend or chat over Zoom, she’ll always hint that she wants to join. She also says I should invite her to more things so that she can meet people. The thing is, I do invite her to a few events each month and we hang out in our apartment, but otherwise I can’t get any space from her. 

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