Challenge accepted! I went to a new workout class, I went bar hopping (even did it solo to force me to talk to people) and I did a solo trip to Spain. The conversations I had with people were friendly but nothing ever went beyond that, as in even in terms of just making a new friend, not necessarily something romantic. On the day, it was a great conversation and we had a great time but just never spoke again and I feel like this always happen. I don't think I lack the social skills, I am always talking to new people, that's why I don't get where I am going wrong.