>>33542725
>Whenever I match with or date someone I fear them losing interest (partially also because of my dating experience) but also I don't want to be overly clingy/annoying so I'm always stressed about messaging them or not.
Yeah that's very normal to feel. For what it's worth, women will view your texts (both content and frequency) contextually in relation to how they perceive you. As in, a confident and an insecure man could text the same things and get a very different response. Once you get to a place where you're confident and it shows, you don't have to worry about this much.

>I do have "close" friends, but I don't even tell them I'm trying to date because I feel ashamed of it at 29 (and they're all married/in relationships).
Dude what? I mean trying to date is better than not dating at all. All you need is their perspective into why you may not be successful. I'm quite certain it's because you aren't confident enough, but you really need them to tell you.

As for gaining confidence, the only way is by practicing. Social skills can be learned and sharpened. The more time I spend with my friends and just outside in general, the more natural I get at talking to people.

I think you would really benefit from some hobbies where you can also meet people