I played hard to get with a Coworker. Should I ask him out?

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song_tothesiren asks:

Basically I am deeply infatuated with a man who I think feels/felt the same way, but I think I ruined it by playing hard to get.

I didn’t jump at the opportunity to hang out with him when he asked, and now I feel like he has given up trying to ask me out. He has always invited me to public/group things though, so I wasn’t 100% sure if he saw them as a date. I think that’s why I put them off. I don’t really know what to do, and I’m not sure if he is even interested in me anymore due to the fact that he thinks I might’ve been sending him mixed signals.

A part of me thinks I just need to put myself out there, but another part of me desperately wants to save myself from embarrassment. I wish I could just tell him how I felt and have it be like a perfect romantic scene in a movie, but I’m scared that reality will be so far from what I’ve imagined that I can’t bring myself to say anything.

Another problem is that we work in the same environment, thought not directly together anymore, which has led to a bit of reluctance on my end. To clarify, if I need to avoid him then it would be very easy to (I don’t really want to go into more detail about this). I’m scared that if I ask him out and he says no, then I will still have to face running into him every now and then.

Demetrius says:

I love this question because it touches on some topics I love discussing: Women taking the initiative and asking a man out and dating coworkers. Two of my absolute favorite dating topics.

First, let’s address taking the initiative and asking him out. I think, no matter the situation, if a straight woman is taking the initiative to ask out a straight man, she already has a leg up on her competition. I’m a pretty decent catch and I would say that 9.9 times out of 10 I’ve always made the first move, and that’s probably true for most men. Making the first move is going to send a very clear message to someone: “I am interested”. The smartest, most socially-intelligent man is often a bit more oblivious about whether or not someone is attracted to him than the average woman, so this will absolutely work in your favor if he’s interested. Being direct is always appreciated…as long as he’s still into you. Yes, being distant might have worked against you, but if he’s still interested (it’s a big if), then asking him out will work in your favor.

Whether or not he’s still interested is a whole other thing entirely. Depending on the person, being told “NO” to a bunch of invites is very often a clear sign that you’re not interested. It’s possible that he was going to ask you out at one of these events and since he missed that shot, he’s categorized you as a platonic connection and moved on. The best way to overcome this is to just be direct and ask him out. Odds are good that he’ll either say yes or no, because at this point you haven’t given him any strong indicators that you’re interested.

Now, that all sounds good, but asking out a coworker is risky business. I’ve talked before about How to ask out a coworker  and that advice still holds up. Before you ask a coworker out, you should figure out the risks, you should approach asking him out with a lot of tact and subtly, you should be discreet if you do start dating, you should take your rejection well (if you get one) and never, ever be pushy. Considering that, you also need to consider what either being rejected by a coworker and what dating a coworker could mean for your working situation. As I said in NPR’s piece on dating coworkers, Love On The Job Can Leave A Lot To Be Desired, you have to consider not only your own reactions to a potential rejection, but also  ”What do people say about me when I’m not here?’‘. You mention the fact that although you work at the same place, you work in different areas. You didn’t get into the detail, but ask yourself: if news got out that you were dating this guy, or got rejected by this guy, would people discussing either one of those bother you? How much of a negative impact would coworkers knowing about who you’re dating or who rejected you bother you all that much. Also try to consider how awkward it would be running into him at work in 3 specific scenarios:

  1. If he rejects you
  2. If you start dating
  3. If you start dating and then break up

Personally, I think I handle those sort of situations well, rejected or not, but maybe you don’t. If you’re wary about asking him out because you can’t handle those 3 situations listed above, or thinking about coworkers might be saying about you, it’s time to move on to the next boy. If you think you can handle it, and the idea of people potentially talking about your love life doesn’t bother you all that much, take a shot and ask him out. Remember, even if you’re rejected at least you have an answer, instead of sitting at home wondering what may have been.

Good Luck Out There.

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