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TIFU: By trying to hook up my female friend with a hot fire fighter

So many years ago like 20 years ago on a weight lifting community when I was a young teenager I befriend a guy who was a few years older then me, approx 5 years older then me. I was 13 he was 18. He gave him a lot of good weight lifting, dieting, advice and we ended up becoming gamer buddies.

Now we drifted apart for a few years and then rekindled our friendship years down the road. Going forward we will call my friend John.

When I was in mid 20s I ended up moving nearby John. I lived in a smaller town about 2 hours from him. And John and I knowing each for over a decade by this point decided to meet up

  • First time I went to go see him, he showed me around his favorite spots, we ended up watching some sports at a sports bar, drinking having a good time etc.

  • Second time John came down to visit me and I borrowed my dads motorcycle and John rode my bike. We smoked together, he went home

  • Third time John said he was going deep sea fishing and a cousin dropped out and if I wanted to come along I could so I did

Well then a high school friend of mine who is this beautiful Asian/American woman (we shall name her Ana) got a job in Johns city. Like this woman was gorgeous. I also knew her type, she liked really musclar guys, guys who loved sports, etc.

Well Ana and I are talking on Facebook and she mentions she's single and I tell her about John, how he's a fire fighter, likes sports, is really in shape, loves to cook, etc. Ana is super excited about John and I think "Why don't I try and hook those two up?"

So I ask her if she'd be interested in meeting John and seeing where things go, she goes YES!

So I message John and I ask one question, "Are you single?" He said "yea" and I leave it at that. So a few weeks later I have some free time coming up and I ask Ana if she'd be up for meeting John, she says absolutely. So I message John and tell him I'm thinking of coming up to his city to meet a high school friend of mine and if he wants to join us. He says yea. So we agree to meet up at a restaurant I know John likes.

Ana and I get there first, and a few minutes later John comes in. Ana whispers to me that I was right on the money and I'm thinking score, John is single, Ana is hot and succesful John going fall for head over heels. We order some drinks, and our dinner, conversation stays pretty light. We decide to go to a bar.

We get to the bar, Ana get somes drinks in her and starts getting hitting on John, she wants him. It takes John a moment and John pulls me aside and asks me "Did you invite me to met your friend cause you wanted us to hook up?" and I go "Yea I did"

John hangs his head low, shakes his head looks back up at me and goes "Dude i'm gay" and I go "What? Your gay?" he goes "Yea I'm gay" and I ask "Why have you never told me?" and he goes "Well...you never asked" and I go "Why haven't you mentioned any of your boyfriends?" and he tells me that most of his boyfriends have been in the closet and they wanted to keep the relationship off social media.

At this point Ana comes over, she's fairly drunk she rubs up on John arm and goes "I really just want you to know your super hot, and I'd love it if you took me to your bed tonight"

John looks at her and goes "Your really pretty, but your not my type" and Ana goes "O you don't like Asians?" he goes "No, I'm gay" Ana is standing there for a moment, processing this information looks at me and goes "You tried to hook me up with a gay guy?" and I respond "I didn't know he was gay"...Ana looks at me and goes "You've known him for like 15 years and you didn't know he was gay?" and I go "Yea..." she goes "O...wow" she thought for a moment and said "Well...I thought I was going hook up with you, so I need a moment I'm going go step outside"

John and I went to our table and had a good talk, he had only come out of the closet shortly after I moved nearby, and knew I was straight and liked being friends with me and didn't want to ruin our friendship over him being gay and I never asked so he never felt the need to tell me he was gay. And to be fair, I didn't care he was gay he is still a cool guy.

Ana comes back after a few minutes, and sits down and goes "Ok, I'm new here...your gay...so we aren't going be hooking up...but like do you where the best place to shop here is?" John laughs and goes "Yea I can show you"

The rest of the night was good, Ana and John are still good friends. Since that night John actually met the man of his dreams, I was supposed to attend his wedding but...COVID19 makes international travel difficult.

And that folks is the story of how I tried to hook up my hot female friend with my hot male friend...and I found out he was gay.

TL:DR Tried to play match maker, found out my friend is gay.

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