He’s Into Me, But Maybe Not? So confused!!

I met someone several months ago (I actually interviewed him, we now work together and I’m his extended boss) and I’m extremely attracted to him. I had a boyfriend then so I never gave it the time of day. A couple of months later (my relationship was nearing the end) we were at a work function and he asked me to go home with him. I said no (painfully) but a few days later said I wouldn’t mind hanging out as friends and he agreed it’d be fun. He never asked to hang out, I ended up inviting him out with some other co-workers and we had a great time. We had a small conversation about my bf at the time and I not working out too well and I was likely going to break things off. At the end of the night he told me he didn’t want to rush me, but he liked me and asked to kiss me. I said I couldn’t but I was very attracted to him and felt something there. I broke it off with my boyfriend 2 days later seeing as I had my eye on someone else and we already weren’t working out.

The new guy was very flirty after we broke up, still didn’t ask to hang out but would text me asking me how I was doing, what I was doing, etc. He’s not much of a texter but still sent messages every now and then. I told him he should come over sometime and he said he’d like that, and to let him know. Well, my breakup ended up being much more intense than anticipated and I got depressed. I didn’t make plans with new guy and felt like I needed time to process. He backed off and didn’t really text much anymore since he found out the breakup was rather ugly.

A few weeks later I started feeling much better and decided I wanted to take it slow with this guy and see how things go. I asked him to talk and he said he was slammed so we talked after work the next day. I told him I’ve been wanting to hang but I needed some space, and didn’t want him to feel like a rebound or that I was using him. He seemed like he completely understood and admitted he didn’t want to overstep. We talked about some stuff and what was going on in his life, and he said he had also been pretty busy and felt like his career was finally taking off, but mentioned “I’m finally going to be busy doing what I want to do, not that I wouldn’t have time for you or anything like that…” so that sort of told me he was thinking about me in his life possibly. I ended up telling him I was okay and would love to see him again. He said of course and we’d reconvene the following week (he went out of town).

Well, we’re midway through the week and he hasn’t said anything about our conversation or hanging out. He hasn’t texted (not that he really was), I made small conversation one night but I didn’t want to text first another time. He gives me a lot of prolonged eye contact and seems to smile a lot still when I’m around, but not as directly flirtatious like telling me how hot I am and such.

I’m not sure what to do. I know he has the confidence to ask me out. I threw the ball in his court so I don’t want to ask him to hang out, but I’m afraid he maybe isn’t as into me anymore. I know it’s intimidating I’m his boss, but he also said it was hot… so I don’t know. I didn’t flirt back much when it was happening because I was sad, but now I’m okay and he’s not really there. It may be all in my head and I just need to prove I am interested, but I feel like I did by having that conversation with him.

Should I wait and see what happens? Send a flirty text to make plans? Ask him if he’s free this weekend in person? I don’t know!