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Waldon agrees that you should take it slow and suggests “low-key interactions such as a daytime study date or tutoring session.” It can be difficult for a shy guy to ask out a girl on an official date, so asking your shy guy to casually hang out clues him in on your interest so he can feel confident to take your interaction to the next level.

How to Ask Him Out If you’re already friends with the shy guy you like, Greif tells collegiettes that while you should be comfortable with initiating a date, you shouldn’t rush things.Because it’s a group event rather than a one-on-one date, this is a low-pressure way for you to get closer to a shy guy.Once again, you help take the pressure off him because you’re the one who initiated the interaction. You probably see him all the time, but you’ve never met him because he won’t introduce himself to you. Shy Guy so you can understand dating from his perspective, and so you know how to bring this potentially amazing boyfriend out of himself. When you see him out with his friends, he’s always laughing and joking.He seems like he’s always having such a great time. One minute he’s confident and bubbly with his friends, then he talks to you and goes into himself, then he goes back to his friends and he’s all energetic and lively again.




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