Go Ask Alex: Can I DM a guy I haven't seen in years?

Got a question that would scandalize your group chat? That’s what this column is for. Go Ask Alex is an anonymous space for queer readers to ask the questions they’re afraid to ask anyone else—about sex, love, life, and everything in between. It’s judgment-free and completely anonymous.

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Hi there, Alex! I’m sitting in front of a computer screen right now agonizing over whether or not I should message a man I was acquainted with years ago.

I always found him to be an interesting person, but when we were acquainted, circumstances were such that we didn’t really get a chance to get to know one another.

Do you perhaps have any advice on reconnecting with people from the past? Have you ever tried to reconnect with someone you didn’t know very well in hopes of making a new friend?

Sincerely,

A Guy Feeling Uncharacteristically Awkward Right Now

Hi, guy!

This is one of the most beautiful questions, and I think it’s one people only really understand after they’ve lived a little. The older I get, the more I remember, miss, and cherish the maybes and might-have-beens — those little fires, people I knew only peripherally but who felt like they could have been more if I’d only been braver.

There are two tough truths here. The first is that there is almost no way to message someone from the past, especially someone you didn’t know well, without it feeling awkward and maybe even a little invasive. The second is that you do have something to lose.

If you carry a fond memory of him, even one tinged with sadness that your connection never became more, that memory is still a gift, and reaching out risks changing it. Some advice-givers would say that if you have no relationship with him now, you have nothing to lose — if he doesn’t answer, you’re no worse off. But that isn’t quite true. Nice memories do matter.

Life is made of connections, and in time, most of those connections become memories. People move, get married, change jobs, and pass in and out of our lives. If you are lucky enough to have a fond memory of someone, that’s one of the little joys that make a life feel rich. So yes, if you send the message and get silence or rejection, that memory may be altered. You have to decide whether that risk is worth taking.

And still, if I had to confess the way I’d go, I’d choose the risk. I’d send the message. Fortune favors the bold.

You asked whether I’ve ever tried to reconnect with someone from my past. In a sense, yes: I’ve received many messages like the one you’re thinking of sending, and I’ve always deeply appreciated them.

I want to be realistic though. Even in a best-case scenario, this probably will not blossom into romance. It likely won’t even blossom into a new friendship unless you two live in the same place, have similar lives, or have some natural reason to keep talking. At best, you should hope for a nice text exchange, maybe a phone call, a brief catch-up, and that’s it. But that’s not nothing.

This question touches something hard about adulthood: Relationships depend more on time, place, money, and circumstance than on chemistry or compatibility. Our jobs shape our schedules, our schedules — and our paychecks — shape our availability, and with families and careers, our lives narrow and widen. All this makes keeping existing friendships and connections hard enough. So for most working adults, the idea of introducing a new one — especially someone from the past, from a time we’ve left behind — will feel like more work than they need right now, one more person calling for their attention.

I have beloved people all over the world whom I sometimes go months and even years without seeing — not because we don’t love each other, but because life is busy and never stops. So yes, the hokey phrases are true: People do come into our lives in seasons. Sometimes the conditions are right for someone, sometimes not.

This person may simply belong to an earlier chapter of your life. It may be that whatever spark existed between you belonged to that time, and trying to reopen it now won’t work. That’s possible. You can’t send this message thinking the risk is nonexistent. It will be awkward. It will likely fail. It may tarnish the memory.

Still, I say it’s worth it.

If he doesn’t respond, he will remain what he is now: someone from your past. You’ll have an answer, and the book will be closed. That hurts, but it’s survivable. We close the book on people all the time. Life requires it. Everyone going through a breakup has to do this eventually. Better to do it gently than to spend years wondering, “What if?”

If he does respond, even if just to say thank you but no thank you, then you will at least know. You will have been brave, and that matters so much. Practicing bravery and rejection makes you better able to do both. In my life, this practice has always led to good things, even if not what I originally wanted.

I’ve appreciated everyone from my past who has reached out. I’ve found them brave and kind for doing so. In the past, I rarely had that bravery myself, but I’ve worked on it. I’ve practiced. I’ve faced rejection. It’s helped me so much.

A lot of people think social confidence is something one has or doesn’t have. It’s not — it’s a skill.

Psychologist Gary W. Lewandowski Jr. writes in Psychology Today that flirting and connection are not inborn talents so much as skills to develop, and that getting better comes through learning and practice, not “natural charm.”

There’s research to back that up. A study by behavioral scientists Nicholas Epley and Juliana Schroeder found that people routinely underestimate how enjoyable conversations with strangers will be, but after trying them, participants reported more positive experiences than expected, and the confidence boost lasts.

If you’re trying to build the courage to reach out to someone — online or in person — start small. At a bar or party, simple things work best: eye contact, a smile, and a direct but gentle opener. Vanessa Van Edwards, founder of Science of People, a website and course that teaches what are commonly referred to as “people skills,” recommends plain, low-stakes ways in, like asking what someone is drinking, complimenting something small, or simply introducing yourself. It sounds embarrassingly simple because it is. Meeting new people does not begin with perfect lines, just small acts of bravery.

When I try to find courage, I think of quotes by figures I love and respect. James Baldwin wrote, “Nothing can be changed until it is faced.” Though he was writing about racism in America, I think it applies just as truthfully to love and friendship: longing and loneliness don’t change until you face them head-on.

In your specific case, the best message is the truth. Not a page of text, just a short paragraph about what you remember of him and why you’re reaching out. Treat it like a polite, kind, one-way letter with no expectation of a reply. You can even admit that you’re nervous about sending it. Vulnerability is brave.

If he’s a good guy, he’ll see the bravery in your message even if he doesn’t want to reconnect. If he doesn’t answer, that’s the answer. A kind person will answer, even if it’s just: “Thank you, but I don’t have the space in my life to build a new connection.” Or: “Sorry, but I’ve left that time in my life behind. I hope you understand.”

Or he might say, “Wow, I’m so glad you reached out! Do you remember that time…?”

Alexander Cheves is a writer and former sex worker who spent more than 12 years in the adult industry. He writes Out’s sex-and-culture column Last Call and is the author of My Love Is a Beast: Confessions (Unbound Edition Press), which Kirkus Reviews called “not for squeamish readers.” In Go Ask Alex, he offers candid advice for readers with real questions they’re afraid to ask anywhere else. Send your question to askbeastly@gmail.com —i t may be answered in a future column.