I [M/late twenties] cant figure out how to be interesting I have - TopicsExpress

I [M/late twenties] cant figure out how to be interesting I have been doing online dating, after having not dated for a number of years. I am on the nerdy side, and a bit scatterbrained, though highly intelligent with good career prospects, I am also significantly overweight, but not sedentary. I have gone out with over six women, and I believe I have tendency to bore them to death. I think I have trouble moving away from safe conversation. By safe conversation, it seems like I have trouble talking in any way that might bring judgment upon me. I am afraid of being boastful, and rely on self-deprication. I also tend second guess what I say while I am saying it. For example, questions like what do you do for fun? tend to make me think about what answer I could give that qualifies as fun, rather than what it is that I enjoy. I spent a number of my formative years either isolated, depressed, or both. Accordingly, I think I never really learned how to relate to people. Does anyone have any advice, resources that they could point me toward?

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