As a gay man, I thought I had everything all in the bag, but as I get over the age of 40, I realize there are lots of things to learn. One mistake I made early on is to take my hookup dates to a restaurant. It felt awkward sometimes to come up with different topics that were interesting and less personal. I found myself feeling insecure because of it. There are many other things that you can do on a date and I guess I wasn't organized enough to consider making other plans so I could have a date where there wasn't so much conversation.
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When making conversation, it is not good to ask direct questions or the conversation will go south. I think it is better to let the person talk by asking a general question. You need to be a better listener too and that is why you must feel this way. I think a restaurant hookup is cool because that is where you iron out all the details so that you can get to know each other better.
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I think you have to be organized when dating anyone. It makes the date go smoother. You can choose other things to do other than go to a restaurant, which is something most people do anyway. Plan a date that is unique to what you like and what the other person likes to do. You have to be very creative when you plan to go out with someone for the first time because you want to make that first good impression.
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You shouldn't feel insecure about asking questions of your date. How are you gonna learn anything if you don't ask questions that you think are very important to you. I guess I am saying that it is OK to ask questions. You want to know and the only way to know about someone is to ask them, right? So just chill out and be OK with eating at a restaurant with a date.
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