2 years later.... should I (26F) /how do I shoot my shot with 25M

cleaning up my iphone photo albums today, came across some food photos i sent to a guy (25M) I matched with on an app almost 2 years ago now. Matched and started talking early 2018. I went back through all our conversations because why not, those food photos were bomb, and now I'm wondering if I should reach out to this guy. I'm terrible over text but he messaged me first, and often, and asked great questions, sometimes texted me multiple messages in a row, and always kept the conversation going. He made suggestions of dates like oh we should do this or this sometime, but never explicitly said hey wanna go do something with me this weekend. Despite that, I've never really connected with someone like this over text and we have the exact same sense of humor, interests, everything. BUT. we texted for almost 2 months and never met up so it kind of just ended up in a mutual ghosting or really just fizzled out. At the time, I was transitioning to a new job and I knew it would require me to move across the country in a year, so I wasn't too bummed and didn't even think to be the one to say hey let's go on a date.

Now it's almost 2 years later and after having many many terrible text and first date conversations, I still haven't found anyone I clicked with in that way and am wondering if there's a way to restart this. this upcoming new year has me feeling old and so over wasting my time now. Who knows if he's even still dating... something in my mind tells me a guy who is that great must be off the market already (had mutual friend with him so can confirm not a catfish but he's pretty cute). It does look like he may have updated his profile on the app somewhat recently (maybe like in the last 6 months...?). I still live across the country, but will be back on a work assignment for 3 months over this upcoming summer. And, in a year and a half will be back in town permanently. My parents also live in town near him and I visit them a few times a year. Maybe none of that is good enough? IDK what to do. Or where to start. Do I reach out? What would I say? Do I wait until I'm in town over the summer to reach out? Or wait til I'm back permanently? Was he never really that interested if he never asked me out on a date? Am I just getting stupidly sentimental because it's about to be 2020? Should I just get over it?

Submitted January 01, 2020 at 12:06AM

cleaning up my iphone photo albums today, came across some food photos i sent to a guy (25M) I matched with on an app almost 2 years ago now. Matched and started talking early 2018. I went back through all our conversations because why not, those food photos were bomb, and now I'm wondering if I should reach out to this guy. I'm terrible over text but he messaged me first, and often, and asked great questions, sometimes texted me multiple messages in a row, and always kept the conversation going. He made suggestions of dates like oh we should do this or this sometime, but never explicitly said hey wanna go do something with me this weekend. Despite that, I've never really connected with someone like this over text and we have the exact same sense of humor, interests, everything. BUT. we texted for almost 2 months and never met up so it kind of just ended up in a mutual ghosting or really just fizzled out. At the time, I was transitioning to a new job and I knew it would require me to move across the country in a year, so I wasn't too bummed and didn't even think to be the one to say hey let's go on a date.Now it's almost 2 years later and after having many many terrible text and first date conversations, I still haven't found anyone I clicked with in that way and am wondering if there's a way to restart this. this upcoming new year has me feeling old and so over wasting my time now. Who knows if he's even still dating... something in my mind tells me a guy who is that great must be off the market already (had mutual friend with him so can confirm not a catfish but he's pretty cute). It does look like he may have updated his profile on the app somewhat recently (maybe like in the last 6 months...?). I still live across the country, but will be back on a work assignment for 3 months over this upcoming summer. And, in a year and a half will be back in town permanently. My parents also live in town near him and I visit them a few times a year. Maybe none of that is good enough? IDK what to do. Or where to start. Do I reach out? What would I say? Do I wait until I'm in town over the summer to reach out? Or wait til I'm back permanently? Was he never really that interested if he never asked me out on a date? Am I just getting stupidly sentimental because it's about to be 2020? Should I just get over it?