Tl;dr I walk dogs in the neighborhood where my high school crush lives. I saw him for the first time in 6 years a few days ago and now I can’t stop thinking about how I can find a non-creepy way to reconnect with him. I occasionally run into a woman I think is his mom. What is the best plan of action you can come up with for me?
Full Context:
I went to middle school and high school with a guy named Matt. High school was a decent sized one, so I’m not even positive he’d remember me (I was that shy smart girl who didn’t talk much), but we did have a lot of the same honors and AP classes, rode the same bus, and talked a few times. I’d say we were acquaintances at the least. I had a little bit of a crush on him throughout those years of school, but I haven’t seen him since we graduated high school.
I’m a dog walker in the neighborhood where I grew up (where my mom still lives, so I use her house as a sort of home base between walks although I don’t live there anymore). I’m out walking around every afternoon, and I’ve met most of the people who live in the area just by running into them. I’m pretty sure I know which house his family lives in, and if I’m right then I’ve met his mom quite a few times. She’s super nice, and even waves at me every time she drives by. I gave her one of my business cards one time so it’s possible my name is on a card on their fridge, who knows. She never told me her name, though, so I never found a way to mention that I may know her son.
Up until 3 days ago I thought he had moved out because I hadn’t seen him in like 6 years. But this week I’m dogsitting for someone in the neighborhood so I’m sleeping at my mom’s house with these dogs. On Monday evening (later in the day than I’m usually around) I drove down the street to get the mail at these dogs’ house and I saw Matt walking home from the train station. I was a little shocked, and I had to do a double take wondering if that was actually him. He was looking up but I’m not sure if he saw me or recognized me. He was even more handsome than he was 6 years ago and some feelings resurfaced.
For some reason the only plan of action that occurred to me was to go get the mail at the same time the next day to see him again. So that’s what I did. This time he wasn’t looking up as I drove by, he was smiling looking down (either listening to something enjoyable in his earbuds or thinking, “WOW, xanderharris_ is driving past me again. How pathetically hilarious.”). He's just so dreamy and I’m afraid I might have been creepily staring at him. So now I know what time he walks home but I feel like if I approach him during this time it will be creepy. Also, I’m usually not even in the neighborhood at that time.
What should my plan of action be? Do I have to just wait and hope I somehow run into him or his mom mentions that she has a son I might know? Hell, I don’t even know if he’s single. I haven’t stayed in contact with anyone from school (I didn’t have many real friends anyway), and I don’t have a Facebook. I do use Instagram and Twitter occasionally but I’m not following anyone from school, nor are they following me. I looked online to see if I could connect with him through some sort of social media but I couldn’t find any trace of him online. Do I have any hope?