Ask Beastly: What About My Old Crush?

Hi there, Beastly!

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 one’s past? Have you ever tried to reconnect with someone you didn’t know very well in hopes of making a new friend?

A Guy Feeling Uncharacteristically Awkward Right Now

P.S. I find your blog to be a breath of fresh air.

I am a lucky man, AGFUARN. Every previous boyfriend has done the work of reaching out, unannounced and unexpected, to reconnect and make amends. And I am so grateful that they did. I imagine this guy will be equally grateful, too.

I understand the person you’re describing isn’t a past boyfriend. This is someone you wanted to know better and missed the chance. That’s at least what your question sounds like. To which I say: Go for it. It might feel strange, and it will be awkward, but what you have to lose is nothing, and what you have to gain is everything.

Be like my exes. Don’t be like me. I assume old flames and past flickers won’t want to talk to me, and I’ve always appreciated people from my past reaching out. I’ve found them to be incredibly brave and kind for doing so.

I don’t have much experience reconnecting with past people, so I don’t know if I can offer much help. And here I must confess one of my worst flaws: I’m a flake. I’m terrible at communication. Out of sight, out of mind. My poor friends may go weeks without hearing from me, just because I forget to text them.

The longterm people in my life know that the work will fall on them to maintain communication. It won’t be me. So reaching out is not my forte.

If you try it and this person from your past doesn’t want to reconnect, you can go about your life without a “what if?” You’ll have your answer, made your attempt, and that will be that. I am plagued by questions about people — guys I should have given more affection and honesty to, friends I should have been more engaged with, and people I wish I had loved more. My “what ifs” are my greatest regrets.

Harvey Milk said this fabulous quote. I can’t find exactly where or when he said it, but the internet seems convinced that he did. It’s beautiful:

Go after her. Fuck, don’t sit there and wait for her to call, go after her because that’s what you should do if you love someone. Don’t wait for them to give you a sign cause it might never come. Don’t let people happen to you, don’t let me happen to you, or her, she’s not a fucking television show or tornado. There are people I might have loved had they gotten on the airplane or run down the street after me or called me up drunk at four in the morning because they need to tell me right now, and because they cannot regret this, and I always thought I’d be the only one doing crazy things for people who would never give enough of a fuck to do it back or to act like idiots or be entirely vulnerable and honest and making someone fall in love with you is easy and flying 3000 miles on four days notice because you can’t just sit there and do nothing and breathe into telephones is not everyone’s idea of love, but it is the way I can recognize it because that is what I do. Go scream it and be with her in meaningful ways because that is beautiful and that is generous and that is what loving someone is. That is raw and that is unguarded, and that is all that is worth anything, really.

Harvey Milk

Send the message.

Love, Beastly

Hope my advice helps. Please tip me or support my work with a monthly donation on Patreon! Every dollar given helps me continue my mission of providing sex-positive information online.Photo by Dhivakaran S from Pexels.


  1. On vacation I met a guy in a pub and one thing led to another which led to an incredible night of fun. After he left I read this post and decided to extend my stay 1 more day so I could see him again. Best decision I’ve ever made! Going back for an extended stay with him soon all thanks to you Beastly.

    Liked by 1 person

      1. I’m flying back on 11/21 for an extended visit with him. He and I are most definitely “going after each other” and it feels incredibly right.
        You have encouraged me through this blog and your articles in the Advocate to be unashamedly and bodily myself, which for years I was deeply afraid to do. You helped me to move beyond acceptance of my sexuality and kinks to celebrating all that makes me, me.
        Thank you again.


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