Here's the Thing: Don't Ask Her Out


About two years ago my long-term relationship ended. She was very respectful and forthright, for which I was grateful, but otherwise devastated — to the point where my self-esteem was shattered (but that's another story).

After a long bout of self-reflection and healing, I'd returned to the dating scene. Throughout this journey I'd met some great people, had wonderful conversations, but felt no real connection.

I've worked at the same company for ten years, and there's this woman whom I regularly have conversations with. We don't work in the same area, but see each other in passing and in the cafeteria.

Every time I see her, she approaches me with a new story about her life, and a smile on her face. She's something of a social butterfly, and knows a lot of people in the building — so isn't uncommon for her to chat up a coworker, but there are often times when she'll make a beeline for me specifically.

We never talk about our dating lives. She can be shy, but also very candid about intimate details of her life.

Until recently, I hadn't considered her as anything other than a work friend, but I think I'm developing a crush. The issue here, is that I can't get a read on her (which is both fascinating and SUPER frustrating!) and how she may view our relationship. There are times where she'll add an intimate piece of information to an otherwise normal conversation. I like to think I'm fairly perceptive when it comes to social cues, and if someone is flirting, but for whatever reason this woman is still a mystery to me!

I know your stance on dating coworkers, but should I really pass up this potential connection?


I could earnestly spend four hours writing out an explanation for writing out why it is that I think you don’t feel a “connection” with people on dates, but neither of us want to spend our time on that, so I’ll try to condense my thoughts into this: dating is artificial as fuuuuuuck. Sitting down with someone you’ve never met before in a nice-ish restaurant and talking about how many siblings you have and where you grew up does— of course— not foster feelings of love or lust all that often. Because it’s a weird fucking thing to do. The only reason we’re still doing it at all is that there aren’t that many better options (or so says society).

The reason you don’t feel anything with anyone on Perfectly Fine Dates is not you and the reason is not the other people. It’s that randomly trying to date a bunch of people over stiff dinners will OF COURSE never* match up to the organic hotness of simply falling for someone in your real life.

Now, on to this particular lady. I don’t have anything against coworkers dating as a theoretical rule. It’s where you meet a lot of people, it makes sense that some people are going to fall for one another. My problem is that short of it sort of happening organically (sorry to keep using that word), the beginning of trying to start said interoffice romance is almost always dicey. See, the problem isn’t dating at work. The problem is asking people out at work because you don’t want people to feel like even at on the job they aren’t safe from others hitting on them.

It is exhausting emotional labor to figure out how to navigate in the workplace around the romantic needs of straight, cis men (you might not be a straight guy, I really don’t know, but straight cis dudes tend to be the largest perpetrators of this). Am I encouraging him if I respond? Am I rude if I don’t? Am I unprofessional for playing along with his flirting even if I don’t want to or am I a bitch if I shoot this down too early? I want to see where this goes, but if I break things off with him or don’t want what he wants, will he become retaliatory? Was I flirting and encouraging this? How do I get him to stop coming over during my lunch hour and talking to me? Of course, there is the possibility for this in all work relationships across gender, but the way the world currently works, it’s mostly the rest of us having to navigate around the unchecked horniness of straight cis dudes.

Frankly, I’m not convinced that this woman is flirting with you; she very well might be, I’m just not sure that she is simply because she shares information with you. I would say the odds are about even here that she’s either flirting politely or just a nice person. Remember that women are TRAINED from a very young age to be hyper-attuned to what men want us to reflect back to them. (Of course, some people are better than others at this—or more interested in doing this—regardless of gender). She may seek you out to talk to, but that might be simply because you haven’t asked her out or been untoward or flirty in any way. She may simply feel at ease around you… almost like… I don’t know… a friend.

Honestly, friendship is the step I think you’re missing, and I don’t fault you for missing it. People often overlook the deep, unmatched gift that is female friendship because women are also hot as shiiiiiiit. I know it’s difficult to imagine but what if— hear me out— you liked someone, enjoyed talking with them, and then just were their friend and you didn’t think that relationship was lesser because a woman didn’t fuck you?

Be honest with yourself— BRUTALLY, EXCRUCIATINGLY SO— about if you feel a connection because you want to fuck her or because you guys actually talk about things you both enjoy. Are you asking her questions? Are you making an effort in the conversation? Or are you just waiting to do enough listening in hopes of filling up some imaginary meter that will ding when she’s ready to fuck you? I cannot tell you the answer, but I can tell you that if you just are attracted to her and don’t think you’d have any interest in being her friend, leave it be. If, however, you genuinely enjoy being around her and wouldn’t be depressed if you two never boned, be her friend. Maybe after doing some good friend work, after seeing her as a PERSON you might want to HANG AROUND WITH and not just “oh she’s nice and I’d like to sexualize and romanticize her kindness,” then you can possibly wade into the idea of dating. Together. Which will make it not creepy and inappropriate for the work place.

To recap: Should you ask her out? No. She’s at work. Should you try to fuck her? No. She’s at work. Should you make an attempt to befriend her if you actually enjoy your time together? Yes. Might that one day lead to dating? Possibly. It also might not!! She might not even see you that way. Trust me, you want someone to be as into dating you as you are to them.

I know you want to date someone. I know that feels validating to you. I know it would feel lovely to have this woman’s lust/love/interest. But that is not her job. The job is yours. Don’t devalue her friendship and coworkership. Enjoy hanging out with her. Invite her along to a platonic event with other people. Get to know her a bit outside of work if she agrees. Back off if she turns you down. If there really is a romantic connection, trust me you two will figure that out. I promise.

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*There are a few stories out there of people who went on a sit-down, real-life date and hit it off, but they are the weirdos/statistical outliers, who are just trying to tell everyone their story so the rest of us waste our time doing sit-down real-life dinner dates while they make out. Don’t believe them.