I've gotten numbers before and have had girlfriends but it's almost always been in situations where I've already gotten to know someone first or the woman has introduced herself first, never a random stranger.

I posted a couple weeks ago on here where I had a very cowardly situation recently and decided I'm going to talk to one woman a day in public.

I've been talking to one woman in public per day but I have been kind of pussying out since a lot of those have just been small-talk questions or giving a compliment in passing.

Today I went down to the waterfront. On the way there, I asked a woman a question, but it was just another 10-second small talk. When I got there, I sat on a bench.

At some point, an old lady came and sat next to me (this is not the cold approach). I decided to strike up a convo with her just to be friendly. It was actually a good convo, I learned some fun facts I didn't know about insects. It also helped me feel a lot more warmed up socially.

Then she left and a girl in her 20s sat down beside me. She was cute white girl. She was also reading on her phone and had earbuds in. However, I kept noticing her looking over to me. However, I was feeling very nervous and awkward with how I could naturally look over at her and start up a convo. My heart was beating super fast. Finally, I tried and asked her a question. However, she just kept looking at her phone. Not sure if she couldn't hear me because of the earbuds or if she was pretending, but I just went back to reading. Then later, I saw her looking my way and I looked over at her, but I froze, didn't say anything, and then she got up and left shortly after.

After she left, a tall, attractive woman sat down with her dog. This time, I decided to just strike up a convo right away since she had a dog and I saw the opportunity.

I started asking her some questions about her dog. One of my big challenges has been figuring out how to segway from questions/compliments to something more personal/fun. I just started asking some different questions, like if she lived around here, where she was from (her accent), whether she liked it here. It did have a bit of an interview vibe, but I threw in some of my opinions, as well as some very light teasing.

It wasn't very flirtatious or anything, but it was easygoing, casual convo. She was laughing and smiling. She wasn't really asking me many questions, in fact I said almost nothing about myself, so I wasn't sure if she was interested or if it was just because I was leading the convo. Either way though, I could tell she was comfortable and figured she could always leave if she wasn't. She seemed really nice and down-to-earth.

Because I was sitting on a bench, I didn't know how to end things naturally. The convo went for about 15-20 minutes. Then, at the end, I just said "Well, I have to go, but would you like to go get coffee sometime?" She said "Sure," put her number in my phone and we said goodbye.

A little after I left, I sent her a text that it was great meeting her. There was no response, so I figured she wasn't interested, but I still felt so great for doing it. It was a huge weight off my shoulders to not be held back by my own limitations.

Then maybe an hour or two later, she texted me back that she just got home and it was nice meeting me, with a smiley face emoji. I'm going to shoot her a text in a couple days to set something up for the weekend.

What I learned:

- The hardest part is starting the convo. Once you do that, the rest is way easier.

- Follow through and don't read into things. With the first girl, I assumed she was ignoring me and psyched myself out. There were a lot of moments I could've done that the second time, but I would've been wrong.

- Worst case scenario is probably that a woman probably finds it awkward. The first girl on the bench probably found it weird when I looked over and didn't say anything or smile, but she left and nothing else happened. It wasn't a big deal.

- There were definitely awkward moments and things I need to work on. However, I would never be able to even know what these are without trying and having the experience first, so now I can handle them more smoothly in the future.

- As well, I think starting up the convo in the first place mitigates a lot of the awkwardness. Because you're doing something many guys don't do, not everything has to be perfect. If I had the same level of just chill, casual conversation over a dating app, it probably would not be as successful.

- Overall, it's not really about getting the number. It's about having fun, becoming better/developing your skills, meeting people, and having new experiences. If you strike up conversations with people, regardless of whether you get a number or not, your day will be better. My day was better for meeting this woman and the old lady too.