Search Results: shy guys flirting relationship

Guy 1 - PROS: I was immediately attracted to him when we first met in April. Physically he's literally everything I've ever asked for. Great personality, kinda shy but fun, into sports, a bit of a party animal, has the perfect sense of humor, is super nice and caring. All that could be said about me too. I think I've been in love with him since June.

CONS: probably likes me as a friend and that's it. He got out of a long term relationship 6 months ago and I can't tell if he's emotionally available or still hurting. Honestly I feel inferior to him.

Guy 2 - PROS: He's the sweetest human being on earth. Definitely into me. Our personalities are very similar too and conversation just flows effortlessly. We flirt a lot and I really can see a connection there. I actually like him a lot.

CONS: he's ugly. I mean, I'm still attracted to him, but his looks are the literal opposite from guy 1. He's been through a terrible breakup 8 months ago. I think he might be idealizing me (he told his friends I had no flaws, was his dream girl etc). I don't think I like him as much as I like guy 1.

So there is this guy at my job who is 30 (I am 23). I have had a crush on him for the better part of 6 years. I was in a long term relationship until a few months ago, and after we broke up my interest was renewed in job guy. He's a pretty shy guy who had a girlfriend a long time ago but who hurt him really bad somehow, and has only gone on a couple of dates since then.

Before, I'll even admit, I was way too young for him, and I had not had any previous relationship experience. Now, I have had a long term relationship under my belt as well as graduated from college, so I feel way more mature. We went to the same college (not at the same time) and are both in a health profession (I am in grad school and he has a full time job). About a month ago (with the coaching of my boss), I texted job guy to see if he would be interested in hanging out. I have attached a screenshot.

I only see him once a week at work, so I've been trying to talk and flirt with him those days. One week we talked about his nephew and how I got my first patient in my field. The next week he was sick and called out and the following week when I came in he was like, "if anyone every offers to give you ____, say NO. Very painful."

I was off this past week, so I had people talk about me while I wasn't there (oh, X is my favorite manager, her hair is so beautiful, I wish she were here, etc) to see if he would react. I snapchatted this one girl and she said when she got it she was like, "OMG, X snapped" and he turned around, and when she asked him if he wanted to be in a group snapchat back, he said he doesn't look good in pics.

So, since it's been a month since I asked him to hang out, I'm just wondering if it would be wise just to text him and say hey or not. Please help!