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One of the easiest ways to be comfortable around that special someone is to spend more time with them. For example, ask them to meet up for a movie marathon or to hang out at the park. When you hang out, wear clothes that you feel comfortable in, which will help you feel more confident around your special someone. Try to talk about the things you normally talk about, like your hobbies, interests, and favorite music, which will help you feel like you’re just talking to a good friend. You can also ask them open-ended questions, like, “Have you been anywhere nice on vacation?” or “What’s your family like?” to get to know them better.
Video: How to Be Comfortable Around That Special Someone - wikiHow