I (18F) play on this tennis team at my school, and this guy (17M) is a manager. We get along, crack jokes and play together a lot, but I wouldn’t say he sees me close enough to be a friend. For example, when we see each other in the hallways, we don’t say hi or anything.

There’s this fair in my town, and I want to ask him to go with me, but I have no idea how. I’ve barely texted him before, and we’ve never hung out alone. I feel like it would be awkward and weird for me to just randomly be like “hey, wanna go to the fair w me?” He’s really shy and oblivious (same as me), so I feel like I would have to be direct, but idk the right message to send.

edit:

do you guys think texting, “hey, this might be random but would you wanna go (to this fair/bowling/etc) with me?” would be a good way to ask? I’ve never done this before, but that feels weird 😭

3 comments
  1. A slow option would be to increase the time and frequency you guys spend together. The more you guys spend time with each other. The more comfortable you guys will be. This will make texting much easier. After some time feeling for each other may blossom but who knows how long that will take. For a fast approach, take the initiative and start making moves on him.

  2. Don’t text him or straight up ask him or play some crazy long game.
    Next time you’re talking to him say ‘hey, have you been to the fair yet? It looks so fun, I really want to go’ and smile at him. If he likes you he’ll invite you and feel all proud of himself for asking you out. If he misses the hint say ‘I was meant to be going with “x” but she can’t go now and I’m so sad I’ll miss it’ he will definitely get this hint, and if he doesn’t you haven’t made things awkward. This is how girls ask guys out. You’re welcome.

    Also, say hi to him in the hall

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