​Ask Dr. Nerdlove: How Do I Ask Out The GameStop Girl?

What's up, Kotaku? Welcome to the latest installment of Ask Dr. NerdLove, the only dating advice column that understands what to do when your prince or princess isn't just in another castle, they're also not returning your calls.

This week, we've got stories of office-fling etiquette and an answer to the burning question: What do you do about your crush on the hot GameStop clerk?

Hey Dr. NerdLove,

So awhile back I was having casual sex with a women I met through some friends (best sex I've ever had actually). Let's call her Jill. After a while she was giving me some hints that she wanted to have a relationship and not just casual sex. But every time I invited her to dinner or going out for drinks or whatever, she would have some excuse to not go. Then we would end up going out with friends again, and end up banging again.

Question 1: What's up with that? Why would she say she wanted more than sex, and then make no effort to do so?

Now, I work with her. After a few weeks, I noticed she was flirting with me pretty heavily. So I asked her to dinner. She blushed and said she wants to, but because we work together, she isn't sure if we should date. But she said "We should at least hang out"

Now she has been asking me like every Friday, "What are you doing this weekend?" I let her know my plans and ask what she's doing. She is usually not doing much. She asks me so often, I figured perhaps she wanted to go out. So I invited her for out for drinks this Friday night (not realizing it was VDay). She says she made anti-Vday plans already. I know for a fact she made these plans with her friend. So she isn't making excuses this time.

Questions 2: Should I ask her again, or am I just wasting my time?

Now the hard part. The women I really want to ask out also works in my office. Let's call her Sally. We flirt all day long. I have a hard fast rule to not ask out or go for any women that haven't made physical contact with me in some way. Sally pushes me if I make a joke about her or walks by my office chair and shakes it to razz me. We have a ton in common and she's really fun to be around. Problem is, Sally became friends with the women I used to have casual sex with, Jill. I feel trapped. Like I can only ask out Jill. I feel like because they are friends, of course they talked, and Sally knows I used to sleep with Jill. I hate it. The first 2 questions wouldn't even be a concern for me except I'm aching for some sex. I don't want to totally screw over my 2 options for it. Problem is I really want to date Sally. And I can tell she wants me to ask her out. WHAT DO I DO!!! AHHH!!!!

~Confused

OK Confused, let's take it step by step here.

So you've got a casual, no-strings-attached fling with Jill and you think you're getting some "let's have a proper relationship" hints from her, but whenever you drop the possibility of going on an actual date… well, she's got an excuse as to why she can't. And while you don't mention it in your letter, it sounds like she's not offering an alternate time when she would be free.

I hope you see where I'm about to go with this.

Here's the NerdLove rule of thumb: once is happenstance. Twice is coincidence. Three times is sending you a message. This applies to unreturned texts, canceled dates and being "busy" when you ask her out.

Hate to tell you this, but she's giving you a pretty clear message: she's cool with the bangin' but she's not actually interested in turning this into a relationship. Why is she dropping "relationship" hints if she's not actually interested? Well, one possibility is that she feels like she should want a relationship… but she doesn't. The cultural narrative is that women are "less interested" in sex than men are - which, incidentally, is complete bullshit - and there's a lot of social pressure to conform to this idea. Women who take ownership of their sexuality - like, say, having a casual fuckbuddy relationship with a guy - tend to get slut-shamed for it. As a result, you get a lot of women who get denigrated by society for what they want and feel pressured to at least pretend that they're looking for something more serious when all they want to do is get some strange, same as guys do.

The other possibility: you're reading things into it that aren't there.

From the sounds of it, everything she's doing - asking you about your weekend plans and what-not - is her being friendly and making standard co-worker chit-chat. She likes you as a person. She enjoys hooking up with you on occasion. But it could be that she really just doesn't want to date.

Sally, on the other hand, certainly seems like she does. So what should you do?

ASK HER OUT ALREADY. Sheesh!

The fact that you've slept with Jill isn't a disqualifier. You're not her possession and people don't get to call dibs on other people. It doesn't matter if Sally knows you used to hook up with Jill. In fact, in many ways, this could be a good thing: you've essentially been pre-vetted as a cool (and bangable) guy by Jill.

So quit making this more complicated than it has to be. If Jill has a problem that her no-strings-attached fuckbuddy is taking advantage of the fact that there are no strings (SPOILER ALERT: she won't) then everyone can put on their grown-up pants and deal with it. This ain't high-school or a dating sim. Ask Sally out. You'll be fine.

Hey Doc,

I've been a frequent customer at my local GameStop for years and have a great rapport with most of the staff there. If I'm in the area and it's not busy, I typically hang out a bit just to chat with the employees about life and things besides video games (never distracting them from work, of course.)

A new girl started there a few months ago and since then I've managed to strike up the same basic rapport... except that she's kind of flirty with me, we have fun and she's really cute. I'd like to ask her out for coffee sometime but I don't want to be THAT PERSON. I'm socially aware enough to recognize that flirtation behind a counter is not necessarily a sign of interest. However, I've paid attention to her interactions with other customers and none seem the same as our own, but that could just be confirmation bias.

So my question is, what is the etiquette regarding asking someone out while they're at work?

Sincerely,

A Consumer

It's generally a bad idea to ask someone out while they're at work.

Here's the thing about asking out people in retail or service industry, whether they're waitstaff, bartenders, baristas or store clerks: they're on the job, and their job requires that they be friendly professionally. Women especially know that being a little flirty can be the extra edge that helps make a sale get a larger tip.

It also means that people mistake their professional flirting for genuine interest. As a result: they get hit on all the damn time. This is why hitting on the waitress or the bartender, or the cute alterna-punk at Starbucks who knows your order by heart, is usually a bad idea. You end up being just one more guy trying to ask her out in a long string of 'em.

And when it's a woman working at a nerd enclave like GameStop, it can be a never-ending rotation of dudes hitting on her and other dudes challenging her nerd cred. This can be exhausting.

Now, keep in mind: people are people and it's not impossible that yes, she digs you.

Here's how you tell the difference between Professional Niceness and genuine interest. Is she going out of her way to talk to you? If things are slow and you're around, does she make a point of coming over to chat, especially about non-gaming topics? Is she asking you questions about you, especially any probing questions about whether you're single or not? Is she making a point to tell you about her life or trying to find commonalities with you without your prompting it? If the answer is "no" then the odds are she may enjoy talking with you as a welcome break from work… but that's it.

All that being said: if you're going to roll the dice, then you need to do it right because otherwise, even if you have the best of intentions, you're just going to be another guy who hits on her while she's at work.

It is possible to hit it off with people who are on the job, whether it's the waitress, the bartender or the store clerk. I've done it several times. It's all in how you do it. The most important thing is to connect with them as an individual - being able to talk with them about themselves without being in the customer/server mode. If you can make that connection, then it's a lot easier to be "the awesome person she wants to get to know" instead of "pick-up attempt #4000 in a series."

You have to be socially well-calibrated, and you have to be able to make it low key in order to avoid making things awkward - especially because it can be super awkward for her to say no while she's on the clock. The first, no-pressure way of asking her out is to invite her to a group thing. "Hey, my friend's band is playing at [place] next [date]. A bunch of us are going; you should come by!" This puts much less pressure on her right then and there, since inviting her to a social gathering is less awkward than a date. If she comes, you can ask her out then, when she's not on the clock.

The other option is to make a low-investment invitation. If you've been having a good, energetic conversation with her - watching for signs of genuine interest and engagement and making sure she's not uncomfortable - then as you're getting ready to leave, tell her, casually, "You know what? I never do this, but you're really cool and I've enjoyed talking to you and I'd like to see you some time. I promise nothing but fun and good conversation. Here's my contact info, hope to hear from you." Then you head out. Will she call? Sometimes. The odds are against you… but then again, they were already pretty damn high to begin with.

The key is to treat it like it's no big deal. If she's into you: awesome! If not: enh, it happens, you just behave exactly as you have before. Don't bring it up, don't try again. By treating it as no biggie, you're able to make things less awkward the next time you see her, letting her feel more comfortable around you.

Good luck!

Have you got stories of illicit work hook-ups? Tales of being hit on while on the job? Share your thoughts in the comments section! And we'll see you in two weeks with more of your questions!


Ask Dr. Nerdlove is Kotaku's bi-weekly advice column for matters of the heart, hosted by the one and only Harris O'Malley, AKA Dr. Nerdlove. Got a question you'd like answered? Write doc@doctornerdlove.com and put "Kotaku" in the subject line. Man, woman, single, married, he's got advice for everyone.

Harris O'Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. He is also a regular guest at One Of Us. He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove. Dr. Nerdlove is not really a doctor.

Top image from Empire Records.