WebApr 22, 2024 · A shy guy will be more likely to engage with you one-on-one. If your friends are around, ask them to meet you later so you can talk in private. Then walk up to your shy guy with a huge smile and say "Hi." 3 Ask open-ended questions to keep conversations going. [4] Greeting one another and making small talk will only get you so far with a shy … WebFeb 4, 2024 · When you start dating a shy guy, make sure not to bombard him with a lot of details about yourself; it could make you seem intimidating, and you want to avoid that. Another tip is not to monopolize the discussion. You can try getting him to participate by asking simple questions.
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