So I (35F) recently connected with a guy (33M) on a friend trip. There was a group of about 8 of us on a three day trip. I’ve known him for over 10 years but not well at all—only in group settings. I actually hadn’t seen him in 7-8 years.
On the trip, I felt a lot of chemistry between us. He is very shy and awkward. He also struggles with anxiety. I believe he even might have some PTSD from serving in the Army. But he’s so smart, funny, sweet and down to earth. He is exactly the type of person I want to date.
I knew I had to make the first move because of the aforementioned awkwardness. He asked me to do a duet with him at karaoke but I knew that was as far as he’d take it. The last night of the trip (after we both had been drinking) I told him I found him attractive. He echoed my sentiments and got very awkward. Then our respective Ubers came and we had to part ways.
The next morning he was completely normal. When we got back into town, he texted me to let me know he made it home safely and said “we’ll always have Montreal.” I reminded him that I just moved back to the area and now we live 15 mins from each other. I said if he wanted to see me again, he could. He said he’d like that very much but he asked me to be patient with him since he was about to start a new position and schedule at work and his life was about to get “chaotic.”
We finish the convo and say our goodnights. I don’t hear from him for 5 days. I texted him just saying hi and hoped his week was going well. We ended up texting all weekend but just surface level stuff. He was being funny and a little flirty. He confirmed he had worked every day since we got back from the trip and it was very stressful. I did tell him I’d love to grab food or drinks sometime. He said “Dinner and drinks? We’re definitely making that happen.”
Sunday night we said our goodnights. Didn’t hear from him for a week.
My friends are telling me to be patient with him since he is awkward and he works a lot. They tell me he is probably intimated by me a bit. They tell me to not project my past experiences with men onto him and to give him some grace. It has now been two weeks today since we returned from the trip.
As a Hail Mary, I asked if he wanted to grab dinner with me this upcoming weekend at a steak house he had told me about. He enthusiastically said “Absolutely! A lovely lady and premium meat. What more could a humble fellow such as I ask for?”
He seems into it. And obviously things will become clearer after dinner this weekend. But I guess I just constantly wonder why hasn’t made ANY moves. I have never had to make this many first moves. My social media feed is inundated with dating coaches saying that when a guy is interested he’ll initiate and leave no question.
My friends are telling me that we don’t know his history with women and that he could be jaded and/or heartbroken which prevents him from really going for it with women. And then there’s just his personality, which is a bit awkward.
I’m feeling a bit foolish that I’ve had to pursue him this much. It makes me question his interest.
Any men that are reading this and feeling like this guy sounds like them?
TL;DR: I’m very interested in a shy guy who says he’s into me but won’t make any actual moves to see me. But acts enthusiastic when I do reach out and when I have tried to set something up. Is it possible he’s into me but too awkward/anxious/self conscious to make any moves?