I’ve (Male 30’s) been on a couple dates with a woman recently. The first one was short with more awkward silence than I’d hoped for. She did agree to a second one shortly after the first, which happened a week after the initial one. There was more conversation and things went slightly better, but the awkwardness was still there. I know I’m sort of awkward and it takes me longer than most people to get comfortable with others, and I’ve been told she’s similar in that fashion and it seems to be the case. I do find her attractive and interesting and because of that I asked her on a third date and she agreed again.

I guess my question is should I tell her it takes me a while to get comfortable with people and that I’d like to continue seeing if we can progress slowly? The first couple times I had all these things I wanted to say and ask and then my mind would just go blank.

Really I’m just looking for some advice in general, because it seems like she’s interested too but is just about as awkward as I am. Dating has always felt like climbing a mountain for me but once I’m comfortable enough to open up it gets so much easier.

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