How can you tell when a guy is flirting out of boredom vs. being sincere about it?

punchxcore
I've been working with a guy for the past, oh, almost month and a half or so, and I started to form a little crush on him basically from the beginning. I was so positive that he liked me cause he always asked me questions about my life and things about me, plus flirted quite a bit, then one of my friends brought up the fact that he could be flirting out of boredom, and I had never really accepted that as a possibility. But the more I thought about it, I realized that could be the case because he has yet to ask me to hang out.

Well, today we were joking around and what not and he said something to me (he made a comment about me having chapped lips cause the summertime does that to me, and kept calling me that for like 10 mins), so I was like, "why do you hate me so much?!" but I said it in a joking way, and he smiled at me, paused and was like, "I don't hate you. I just get soo bored at work and I need some entertainment"

I get that guys flirt out of boredom. I really do. However, what I can not quite seem to wrap my head around is the fact that he SHAMELESSLY flirts with me, AND continues to ask me questions regarding my life. Like, what are your hobbies?, what does a vet tech do?, what kind of concerts do you go to?, what are you going to do after you graduate?, etc. And today AGAIN, he asked me how much longer I had to wear my braces for, even though he just asked me that same question like a week ago.

If he were flirting with me and wasn't taking any kind of interest in my life, I would shrug it off, but that's not the case. Seriously, how is one supposed to tell if someone is just flirting out of boredom or if they're flirting because they actually like you, without driving yourself off a cliff. Because this guy is seriously making me crazy. damned if I do, damned if I don't.
How can you tell when a guy is flirting out of boredom vs. being sincere about it?
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