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It sounds to me like maybe these people sense you are trying too hard, and so there's no feeling of connection, so then they don't notice you or have interest in speaking to you when they see you next.

In relationships there's what's said, and also what's felt. Ideally for you to be successful you want to experience a feeling of connection, of relating with the other person. One way to do this is to talk about things you are interested in, that they are also involved in, shared interests. This creates a chance to form some connection.

If you're feeling you don't have experiences, you could try to connect with the person, by asking your questions about them, and then when they tell you an interesting experience they've had, you could admit, "I've never done that, that sounds so fun. I'm a bit less active and I regret that I miss out on enjoying some more exciting experiences. But I'm just more of a quiet, nonadventurous type I guess." Oh and how about: "I really enjoy hearing about your experiences, though. It's interesting." You need to share something about yourself, to make a connection.

The goal is to form some feeling of connection with the person, this creates a relationship.
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