There's this guy at work that I really like, and I think he feels the same way but I'm not sure. He's a year older than me (I'm 19, he's 20), and he’s a manager at the place [where] I work, but we get along really well. My coworkers have said he does treat me different from everyone else, and whenever we're near each other or talking, they start giggling and making comments, so I don't know if he said something because they said they would set me up with him. He's really sweet and a dork, but I've never dated and I'm shy so I'm afraid to ask him even to hang out – not that he’s mean, but it could be weird if he knew my feelings and [didn’t] return them. He does call me “girly,” “sweetheart” and “darling” and he usually only says it to me (he calls every other girl “girly” though). Is he just really comfortable around me because I don’t throw myself at him like all the other girls do, or because he wants to be more than friends? – Confused in Florida
This is always a tricky situation, Florida.
On one hand, you have the potentially super-awkward issue of dating a coworker. On the other, you don’t even know if that’s something he wants. In this way, you’re almost d*mned if you do, d*mned if you don’t.
My advice to you is to keep talking to him. Don’t throw yourself at him, because he may very well be interested in you because you don’t do that (among other reasons, I’m sure). Just keep talking to him and maybe up the flirtation a notch or two. Show him you’re interested in subtle ways like touching his arm or shooting him a random smile.
I can’t tell you for sure if he’s interested in dating, but calling a girl by those kinds of pet names usually means he’s got some sort of attraction to you (I’m more of a “babe” or “sweetheart” kind of guy, though I’m told the latter of those two can come off as condescending sometimes… whoops!). How does he look at you? Do you catch him stealing glances at you every now and then? Does he aim to get your attention over any other girl’s? These aren’t guaranteed signs that he’s interested, but more often than not they tend to be.
If you want to play the situation out, keep flirting and see if you can get a better grasp on how he’s feeling about the whole thing. If he sees you in that light, he’ll come around eventually. As to when exactly you should pop the question… you know, I can’t tell you that. That’s a gut instinct. When you feel like you’ve reached the make-or-break moment of flirtation, that’s when I think you should do it. There isn’t some “set in stone” timeframe, though.
But let’s say you do ask him to hang out or go out on a date and he says yes. That’s obviously the positive reaction because it confirms that he’s into you. Maybe you go grab lunch, maybe a movie (cliché as all get-out, but hey, who am I to tell you what to do?) or maybe you go to a party. Whatever the choice, you want him to say yes. There are no surefire ways to guarantee that answer, though, so your best bet — should you choose to make the first move — is to be sweet about it. Make it casual, nothing too serious. Something like, “I know we work together, but I was wondering if you’d like to…” would acknowledge that you’re coworkers but also acknowledges that you’re both human beings with normal human feelings. You like the guy and you want to go out. Like I said, keep it simple and casual and you should be okay.
On the flipside, let’s say you ask him out and he says no. Don’t be too alarmed and don’t get frustrated or angry with him. It’s easy to confuse feelings sometimes. There are still times when I’m not sure if my barista is flirting with me or just being nice to me! If he says no, just take it in stride. Maybe he doesn’t see you that way or maybe he doesn’t want to make things awkward at work. While they may still be awkward for a few days, that doesn’t mean that you two can’t be friendly coworkers. If he says no, I promise that you will recover. There are worse things in life.
If he says no, don’t get upset with him. Don’t take a few days off to avoid him. Don’t quit your job (I’ve seen it happen in situations like these and people almost always regret that decision). Accept that some people just aren’t “meant” to go out, and respect his decision and the reasons behind it. Whatever you do, don’t press the issue and try to convince him to go out with you — that is guaranteed to make things ridiculously awkward.
Now the only issue is who should ask whom out. While it’s entirely up to you, I think you should go for it.