Worried about dating a friend who had a crush on a female coworker

have feelings for a friend/co-worker (we're both cashiers) that I've known for 2 months. The good news, he explicitly told me that he liked me as well and wanted to move forward. I, however, wanted to see how things go between us before becoming exclusive. I was excited, at first, about possibly starting my first relationship ever, but my insecurities eventually snuck up on me and now I can't stop overthinking.

Context: when I was still in that early stage of does-he-like-me-does-he-not, I asked who he liked at the moment. He told me that he liked our not-so-single female supervisor, but was happy being good friends with her. Few days later, he came clean about it and admitted that he lied because he panicked, but felt incredibly guilty for lying to me (he was so nervous about my reaction that he didn't eat anything and was almost on the verge of crying before seeing me).

BUT, he also admitted that he used to have a crush on said supervisor a year ago. She had a boyfriend at the time (still does). He also had a crush on a different female supervisor, whom he's known since high school, but knew he never had a chance with her because she had a boyfriend. He doesn't think they'll break up anytime soon bc they've been together for so long.

Tell me if I'm crazy, but I'm almost 90% certain that he might have unhidden feelings for the first girl I mentioned. It's this weird, paranoid feeling I have. I suspected that he liked her (based on just one interaction they had - it wasn't flirty, but I was convinced that he liked her just because he was friendly to her) and was partially right about that, so I could be right about this. It doesn't help that she's attractive, skinny, and seems to have an okay personality (don't really know her all that well). When I first met her I was instantly intimidated by her. To be clear, I do NOT hate her.

But I digress. My dilemma is this. I really like my friend. He's quirky, kind, and warm. Makes me smile without even trying. In fact, I think I might even like him more than he "likes" me (does he really, though?) and that's kind of scary. If I'm way more emotionally attached to him than he is with me and it turns out that he actually did have feelings for our coworker, it would probably destroy me. I don't want to be romantically involved with someone who might have unhidden feelings for someone else. What's worse, he might not even know it. I don't want to risk getting hurt by putting myself in a situation where I might be someone's "second choice."

From what I know, the only thing that's preventing him from pursuing this girl is her dating availability. But what if she were single? And even if she continued to date her current bf, how am I supposed to know if he's okay with that? He had a "crush" on her a year ago, but crushes either fade away or develop into something more. But if you have a crush on someone and still have to see them at work all the time, how can those feelings just go away? He probably thinks he's over it, but what if he's not?

I'm so insecure and paralyzed by my concerns that it's uncomfortable seeing her at work. Or even hearing her name. It doesn't affect my work performance, but I get this sick feeling in my stomach. Because at the end of the day, he set the bar high for me. Though he never dated her, he had a crush on her. I'm nothing like her. It's mind-boggling to me that he would even be interested in someone like me. He claims that he likes me because I'm cool, he likes spending time with me, and we share a few common interests. But, really? What if he only feels that way because I'm the only girl who's ever shown interest in his interests? He has a lot of passions and I like talking about them with him and I appreciate those interests, but that's it. What's so special about that?

He assured me that what he feels for me isn't a mere crush. That he's never felt an emotional connection with his other female friends. The last time he ever liked a girl was when he liked someone from his class, I believe, and she had a boyfriend whom she stayed with despite him cheating on her. He was so heartbroken that he had to drop out of his classes. I bring this up because I don't know if he's felt that way towards our coworker. If he did, he never mentioned it. And I don't want to keep digging into his romantic past so I'm left to just make assumptions. A few months ago, I remember one time hearing that she and some other coworkers were going to grab a drink, but he couldn't come. Was it because he didn't want to see her and her bf? Who knows?

Also, he's worked at his current job for 2 years, but only started crushing on her a year later. How intense were these feelings? When did they start, when they fade away (if they did, but again, I'm worried that they're still there)? The thing is, not knowing makes me miserable. But would knowing change anything? What if he really did like her for a long time and had a hard time seeing her because of it?

You know what's also scary? The possibility of her liking him as well. Yes, she has a boyfriend, but because my friend gets along with everyone, I wouldn't be surprised if she found him attractive as well. Idk.

Other relevant info:

-He's never dated before. I've never dated anyone either. This is new territory. What if he wants to pursue something romantic with me only because I'm the only available girl who's shown interest in him? And not because he actually likes me? Cause, you know, some people don't want to single and alone and they'd rather be in a relationship that they may not be fully and emotionally invested in because of that fear.

-He asked her for a ride home after work because it had been pouring outside. Could have been a harmless request bc he didn't want to pay for an uber just to get to his house that was only a five minute drive away...or maybe he secretly wanted to spend extra time with her.

-He had been trying to get me to whistle and I would refuse every time. But one time he commented that she was like that too. This probably means nothing right?

-He brought his parents to our workplace and purposely chose to go through my lane on one of our busiest days. He's normally the one that buys groceries for his family, so this made me think that he wanted them to see me. Which makes me think that maybe he does truly like me. He also suggested that I come with his father and sister to pick him up from the airport when he's back from his trip to see his relatives. He does that a lot, encouraging and inviting me to do things that might be out of my comfort zone.

-He's an extroverted, social Aspie, which I don't mind. It's just, we're such different people. I'm introverted, reserved, and somewhat shy. An anxious overthinker. I don't think I'm a catch at all. So it's weird that he'd find me attractive. It's not based on physical appearance, that's for sure. I feel like he's too good for me because he's such a nice person and gets along with a lot of people. Perhaps that's a little intimidating bc that's something I struggle with. What could I possibly offer if we were to get into a relationship? Maybe I'll ask him that when he comes back just to see his side of things.

I don't have much evidence to support my suspicions that he might like her. Everything is just based on isolated events and gut feelings. I need some clarity and objectivity here. Are my insecurities clouding my ability to perceive things as is? Are they misconstruing bits and pieces of a puzzle I can't fully see?

Sorry for the lengthy post. It just goes to show that my headspace is too cluttered and cramped because of all these thoughts.

I’m telling your right now. Do not do this. Check my posts. I just got dumped by my ex of 3 1/2 years and we work together. Left me for another girl at work. Save yourself the heartache.

You are overthinking everything and working yourself into a frenzy. Just because there is an attraction and a crush does not mean anyone will actually act on it or that they even want to. You need to stop obsessing over this line of thinking. If you're going to make assumptions, make an assumption that he is *not* into this supervisor, but rather he's into YOU. Revamp your thinking. Don't go straight for the negative. Unless you're witnessing flirty behavior, all he is doing is talking to her or asking for a ride. Hell, I've given rides before because they're on the way home, both male and female. It's just a ride. No ulterior motives there.

Emotional attachment with someone who is "on the spectrum" - that's a different issue, and his expression of such will be different than someone who's neurotypical, and I suggest you do some reading to learn to work with it instead of against it. I can't imagine it's easy. All relationships will have this type of clash, but you're dealing with someone whose brain is wired differently, so it's an extra hurdle. Men will often exhibit less attachment outwardly, when inside, they're going through the same insecurities and feelings as you. This is a common complaint of women for years. I'm sure you're already aware.

It's really hard to say if this guy is exhibiting warning behavior because of your sheer paranoia and self-deprication and assuming the worst just because the guy is friendly. Without obvious flirtatious behavior, which you do not describe, I just can't lean in the direction that he's going to dump you the second this supervisor is single. Relationships and dating are a risk. You have no idea if anyone is going to leave or decide they want someone else. If you behave defensively as if you're expecting them to leave or they're panting at every woman they see and know, you will eventually sink the relationship all on your own.

Also, don't ask about past relationships and dig into the details. When you asked about his work crushes, were you expecting or hoping he'd admit out loud he had a crush on you? He made a mistake in sharing his crush, but perhaps at the time he didn't see you as more than a friend at work or he was too embarrassed to say that he had a crush on you because he didn't know your feelings. Who, if they're interested in someone, asks them about their prospects with someone else? Don't ask and then turn it into an issue when he responds truthfully. This will only breed anxiety and jealousy. Everyone has a past, and the older you get, the more of a past there is, and you'll be far better off if you learn to accept this and not compare or fret over it.

Enjoy your time and see where it goes. If you truly suspect there's some hanky-panky going on, then break up now before it gets worse for you.

Start going out on one-on-on dates and see what happens. Stop asking silly questions about other coworkers, crushes, etc. Has he asked you out?