Shy guy — interested or just not that into me?

[peetaspitas]

So there's this guy I briefly worked with last summer. He was always very shy, but I'd catch him looking at me, and I'd felt a vibe there from him. At the same time, I wasn't interested, so I didn't think much of it. He was only around for a few months, but then he came back full-time a few months ago. He shot me a message that he was back, and we went out for drinks shortly after to celebrate (although a mutual friend invited himself and dominated the evening, so that was a bust). I've now developed a genuine "crush" on him. He still does the staring, there's still that vibe - at least I feel something.

 

But. He's quite passive, very shy, very quiet. I'm not these things, and I've been told that I can be a bit intimidating with men and my approach. I flirt with him, idk if I scare him away or not. He's flirted here and there when he's gotten some alcohol in him. Long story short, I directly asked him out a few weeks ago, making it clear that it would be a date. He agreed at the time and seemed interested. A couple days before said date, neither of us having acknowledged it just yet, he messages a few of our mutual work friends to spend that day together instead (we had all discussed a night to hang out the following week, and he either misunderstood my asking him out as a friend night or did a pretty solid swerve away from me). I felt like this was a pretty solid rejection (since my asking him out was very clear), so didn't say a thing, and we ended up spending what would've been a date out with our friends. Sigh.

 

A mutual friend of ours noticed this and said he's just too quiet, you need to take him out after work, he probably didn't get the signs. How much clearer can I be?

 

Since then, we've been messaging each other on a regular basis, which itself is tough because he's not much of a texter, though he often initiates the conversation. Two weeks ago, we had a staff drinks night. It ended early, so the two of us went off to get drinks together. He opened up a lot, spoke a lot, hours went by easily. He ended up paying for my drinks, which was surprising from him, I didn't expect that. When I asked why, he grinned and said "for reasons." Hm. Ok.

 

I went to a party of his a week later, had a great time, he was especially verbal about me to his friends that night. We then made plans to go to a concert the other night, kind of a work event, and another friend of ours ended up inviting herself and coming along. Again, out of the blue, he paid for my drinks and was a bit flirty towards the end of the night.

 

But I don't know if I'm seeing signs where there aren't any. Does he need me to directly say I LIKE YOU, is he too passive or, is he just not that into me?

 

Would appreciate any insight, thanks, everyone!

[Herbalist]

Sounds like he may just be the cautious / take it slow sort in addition to a little shy. He might also not be used to a more aggressive/leader type woman, and it sounds like he may be tickled by it but also in uncharted waters for him.

 

If you're really interested in him then I'd say just keep going with the flow for a bit, especially if he seems genuine (an dnot fake nice) and to have high quality of character. Guys like that are worth the patience.

[preraph]

He's not really interested in you romantically. Or he wouldn't have turned it into a group date. Plus you're flirted and he hasn't responded. He doesn't want you romantically.

[peetaspitas]

Sounds like he may just be the cautious / take it slow sort in addition to a little shy. He might also not be used to a more aggressive/leader type woman, and it sounds like he may be tickled by it but also in uncharted waters for him.

 

If you're really interested in him then I'd say just keep going with the flow for a bit, especially if he seems genuine (an dnot fake nice) and to have high quality of character. Guys like that are worth the patience.

 

Thank you, this is solid advice! And also what my friends have echoed and what's felt right. He does feel like someone worth having the patience for, but I also won't hoist my expectations on to anything. Appreciate it!

[peetaspitas]

He's not really interested in you romantically. Or he wouldn't have turned it into a group date. Plus you're flirted and he hasn't responded. He doesn't want you romantically.

 

Thank you as well! He actually has flirted back, which is the confusing part. But I'm hearing both sides and not banking on anything. It's the group date swerve that seems the biggest tip off, alas.