Best way to approach dating?

7 Comments

I'm a high school senior, 18, male, gay. He's the same age.

I'd like to start dating him, but am unsure where to start.

I've known him since we were freshmen, he's a good friend, but we aren't close to best friends. I've always considered him as someone I'd like to date, but I wasn't as close to him at the time.

I know for certain that he's gay. I am mostly sure he is single. I am unsure if he's attracted to me.

I'm a bit socially awkward, and I don't want to force him, or feel bad for me if he says no. I've never dated someone before, and I'm really unsure as to how it all comes together.

This year I've said to myself that I'll be more out there, and make more friends. I see this as a part of that, but that's not the only reason I like him.

I'm currently "in the closet". Nobody has asked me, so I'd feel extra embarrass bring it up unannounced. He may suspect I'm gay because of the way I act/dress, and because of my long hair.

I have an email of his, so I want to bring it up there, just not as the first topic of conversation. Any ideas what to say, to let him know I'm interested, without asking outright?

Thanks for listening to this ramble. Let me know your ideas and suggestions.

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Comments ( 7 )
  • Mike-Segacamp-Campbell
    5 years ago

    Well, in that case just invite him out for lunch. Make sure it's lunch and not dinner. Dinner is too formal. If he accepts an invitation to lunch, you're good to go.

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  • JOY_DOPAMINE
    5 years ago

    You have to invite him somehow to hang out more, so it's gonna be easy for you to talk about things like this, maybe ask him about his previous relationships, like this you can be sure, unless he's not out yet like you and switch genders of his ex (lol i used to do that when i don't want the person to know i'm gay).

    You can't be sure if he's attracted to you if he doesn't even know if you're gay, maybe telling him is a good start for that, then, just him out for a dinner or lunch and it's gonna be obvious you're into him. Rejection is also FINE.

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    • Anonymous Post Author
      5 years ago

      This is actually good advice. Since I've posted this, I've been hanging out with him more, and getting to know him.

      Yesterday, I spoke with another friend, and he told me to go for it. I'm going to try and be direct with him, let him know how I feel. The worst outcome is just a no.

      There's some other drama involved, but my best solution is just to be transparent. Wish me luck!

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  • Tigernormal
    5 years ago

    Don’t date someone at work or school as if you screw up you have to see them daily.

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  • JacksonPolyp
    5 years ago

    Dudes are horny. If you're certain he is gay it should be easy.

    Just make sure you put spaces between every sentence when you

    text him. That way he for sure sees your simple inquiry of,

    "wanna fuck"?

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  • Mike-Segacamp-Campbell
    5 years ago

    How do you know he's gay? You have to make sure he's gay first or it will be very awkward. It reminds me of something by Grandpa used to always say to me when I was a kid. He'd say "Mike, if you ever assume I'm gay, I'm going to drive you to the laundromat in Springton and sell you to the transients for dryer change."

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    • Anonymous Post Author
      5 years ago

      That's quite the saying! But yes, I am 100% sure. He makes jokes about himself being gay occasionally.

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