So, I have dated dominant, assertive, borderline arrogant men in the past. I didn’t have to give them much indication when I was ready to have sex with them, they’d just initiate and back off if I didn’t respond well or said no.
I’m talking to/seeing this guy I met in my everyday life, organically, no dating apps. And I am so shy with him, and he’s so shy and gentle with me. He’s good to the core– just so sweet and wholesome. I’m sure he does and I’m wrong, but I get the sense that he never thinks about sex.
But…I’m ready. I want him. I don’t know what to do. Should I invite him over late at night for a movie and cuddle up and see what happens? Do I straight up ask him? Do I just break the touch barrier more and hope he gets the idea? I don’t really like to initiate, I’d rather let him do it.
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You’re going to have to do the imitating here. If he doesn’t pick up on stuff you might want to have condoms on hand. And then communicate with him how he can initiate with you.
I think the cuddling move is a good idea.
Communication is key. Be honest about what you want
Just be direct.
Shy guys like the gentle but direct approach. Don’t trap him into a potentially awkward situation; just tell him that you like him and want him. See how he responds. More that likely he’s into you.
Speaking from experience, there is no length, no amount of “hinting” that a shy person will be unable to explain away as innocuous. I have so many stories. You get what you pay for, you hint, nothing happens, mark my words if you’re painting the right picture. It can be discombobulating to just outright say what you want, and also is one of the most precious aspects in any relationship.
Think of the open ocean. How many rotting ships lie at her depths, her crew the same, as certain as can be that signals aren’t necessary, no need to blow the whistle, the ship is hundreds of feet long, sails that touch the clouds, it would be ridiculous to think a ship on an intercept course wouldn’t see you. They have crows nests, scopes, oceanic charts, of course they’ll be looking!
Didn’t think I was going with a nautical theme, but here we are.
Invite him over for that movie night, cuddle up on the couch, and see how it goes. Once you are making out then as “would you like to move to the bedroom?” super sexy and no misunderstandings will happen