A few weeks ago I met a guy at the bar and we agreed to hang out sometime. We finally hung out last night and boy was I rusty. I work fully remote at a pretty easy job and found myself not really having much to say. I do have interesting stories and have lots of fun hobbies, but I realized how not having lots of daily interaction had made me regress a lot socially. Today I decided to get out of my shell and start talking to at least 5 strangers.

I went out with specific intent on talking to strangers, but was super anxious to even begin. This is when I realized how much I need to overcome if I'm ever going to get the dating life I want. I walked around for about 40 minutes before I could even start up a conversation with anyone. Eventually, I went to the local park and felt it would be easy to start a convo by talking about someone's dog.

1 - There was an old lady at a bench with her dog and I went up and asked to pet it. I made small talk about what the dogs name was, how old it was, and all the basic stuff you ask. She seemed really happy to talk about her dog and it felt like a huge anchor was taken off my chest.

2 - This was another lady sitting at a bench who was watching her kid. Once again, I started by asking about the dog and if I could pet. This convo went on for about a minute and she also seemed to like sharing about the pet. At this point, I'm feeling better about being social and feel like the worst of my fears are over.

3 - I see 2 business dudes walking my way and ask where they got the starbucks they're holding. They explain to me they actually got it blocks away and I thank them anyways. Short and too the point, but I'm feeling better at this point. Everyone has been super cool about me stopping to talk to them.

4 - This is another older woman sitting with her dog. I once again ask to pet and start asking her the usual questions, and am surprised as she starts asking me questions back. We talk for about 2 minutes about our dogs and I say goodbye. This was actually a very pleasant conversation and now, I'm feeling good about myself. I only have 1 more approach to go and I decide that I should approach an attractive girl as that's where the majority of my fear lies.

5 - I see a very pretty woman holding a salad at the the stoplight next to me. I turn to her and ask her where she got it from. She is nice and tells, so I turn to walk that way. As I'm walking away, I turn and compliment the boots she's wearing. She says thank you and I head off feeling really good.

I know these are all really basic and none are real "cold approaches", but it definitely felt like I was getting out of my comfort zone. I was starting up convos with strangers and actually enjoying them and I feel like I just leaped over a huge mental hurdle in my way. I felt a lot more sociable when it was done and talking to strangers all the way back on my way home. I think this is going to become a daily thing for me in order to keep me socially sharp and help me work on progressive desensitization. Whether it's an inch or a mile, progress is progress.