Ask Dr. NerdLove: Should I Ask Out The Worker At Cheesecake Factory?

Ask Dr. NerdLove: Should I Ask Out The Worker At Cheesecake Factory?
Image: Shutterstock

Hello, all you sexy angels of the Abyss, and welcome to Ask Dr. NerdLove, the only advice column that can help you manage your relationships in real life AND in Animal Crossing.

We may be under self-isolation and social distancing, but just because life is on pause doesn’t mean that love is too. Sometimes love in the time of COVID-19 means new and different challenges for love, sex and dating. What do you do when you’re a gig driver for a delivery app and you’re starting to get a crush on an essential restaurant worker? How do you ask someone in the service industry out on a date when they’re on the job”¦ even during the coronavirus crisis? How do you get over a break-up when you have to hide the fact that you were in that relationship in the first place? And where does a young geeky man find geeky women to date when their country is under lockdown?

It’s time for the bells and the bees and cutting down trees. Let’s do this.

Dear Dr. NerdLove,

I’ve been delivering food for several apps as an independent contractor. I have a reasonably large area to deliver to but we’re very close to a Cheesecake Factory, where I frequently pick up delivery orders.

I can get the offers daily if I choose as I’m less than a mile from where the restaurant is located.

There’s an employee who works behind the pickup/cheesecake counter that hands the delivery drivers food that I’ve grown quite attracted to.

I’m there quite often and feel like she likely has recognised me as a regular driver coming in to pick up someone’s order.

We have very short interactions typically so there’s no real way to gauge any attraction from her end at least right now.

However as “essential employees” right now we may see much more of each other. Our city has ordered mandatory lock down except for necessary workers.

Normally when a customer hits on an employee there is the issue of the employee not being able to escape and you essentially having a captive audience being forced by the need to make an hourly wage to withstand customer advances.

My desperate nature makes me hope that in the next month me being one of the only people this person sees at work makes it less strange to eventually propose a coffee date.

Date Dash and PostMates

You hit it on the head, DDaPM: hitting on someone on the job is a bad idea as a general rule. First, there’s the fact that, as you said: employees in the service industry”especially attractive women and femme-presenting folks” have to deal with thirsty dudes hitting on them all the time at work.

This results in a two-fold problem.

The first is that you end up being just one more guy in a string of guys who hit on them at work. And while you may be different”hell, you may be a serious upgrade from most of the folks who’ve been trying to get a date out of her”you’re still ultimately going to be at a disadvantage because of the sins of others.

That alone means you’d be facing an uphill climb.

But then there’s the fact that more often than not, the women being hit on have to grin and put up with it because they’re rarely in a position of being able to turn someone down directly and keep their job. Plenty of waitresses, bartenders, shot girls, gogo dancers and others have had folks hit on them and lose their shit when they’re told “no, thanks.” Many of them have even lost their jobs because of it. They may not have been the person causing the scene, but they get punished for it regardless.

This makes hitting on somebody at work a very bad idea. Can it be done? Yes, in theory. Can it be done by you? Unless you’re socially well-calibrated and good at flirting and building attraction“¦ honestly, the odds are against you. Especially right now.

Here’s the thing: you are decidedly putting the cart before the horse, DDaPM. Your attraction to her is entirely one-sided, and you’re not in a position to be able to shift that.

One of the keys to building attraction, especially when you’re talking about somebody in the service industry, is propinquity. As any advertising executive can tell you, being exposed to something repeatedly over time helps increase both familiarity and fondness. This is why the people who do successfully hook up with waitstaff, bartenders or other service industry folks tend to be regulars, folks whom they see frequently and have repeated interactions with them. The more they see that person, the easier it is to have conversations that go beyond taking their order or the usual server/customer chit-chat.

You don’t have that option in this case. You’ve only had very brief interactions with her before the lockdown. That’s not going to improve afterwards; being a delivery driver during the COVID-19 crisis isn’t going to give you more time to hang around and make conversation.

On top of that, you’re doing a decent amount of projecting onto her. You’re working under the assumption that you’ve stood out as a frequent driver, despite the number of folks who likely pick up orders from the restaurant under normal circumstances and the fact that you’ve had very few meaningful interactions.

That sounds a lot like letting your dick do the rationalizing to me. Doubly so considering that you describe yourself as being of a “desperate nature” and hoping that this crisis is gonna cut down on your potential competition for her attention.

That ain’t a good look on you, chief. And honestly, hanging around the vicinity in hopes of getting more delivery orders from that specific restaurant comes a little too close to obsessively hanging around, say, Gamestop in order to flirt with someone who works there for my taste.

And, frankly, acting like this and potentially making her really uncomfortable is a great way for you to lose your job in the process.

I think you’re putting too much hope on an incredibly unlikely sequence of events that has a far higher likelihood of blowing up in your face. If you’re hoping to find a date or a relationship during the pandemic, you’d do far better to polish up your dating app profile and start trying to meet some folks on Tinder or Hinge instead.

Good luck.

Dear Dr. NerdLove,

You get this all the time but I’m a long time reader, but this is my first time reaching out.

So I’ve been with my boyfriend since 2008, when I was 17 and he was 27 (I may not have been entirely truthful about my age when we started seeing each other).He was my first everything, boyfriend, kiss, etc. I thought we had the perfect relationship for a long time, we seemed like the couple everyone wanted to be.

But a few years into our relationship I started taking medication and began to gain weight as a result, about 30 pounds and our physical intimacy all but stopped. He made it clear that he’s disappointed in my appearance and is less attracted to me now. We have sex maybe once a year or so but we’ve gone over two years at times. Even when we do I feel so self conscious during it that I can’t fully enjoy it. I do think I still love him and we’ve built our lives together so I want to make it work between us.

I’ve been attracted to a co-worker of mine for nearly a year now, who happens to be married with children. We hit it off as soon as we met, seemed to click in every possible way. Recently he noticed that I was a bit upset at work and got very concerned about me, he took me out after work and listened to all my problems and shared some of his. We connected on a whole new level when we learned about our similar trauma.

About a month ago we were messaging each other and he was joke flirting, I told him we should stop because I was developing feelings for him, he was shocked and apologised. We continued to talk and we ended up flirting again soon after, one thing led to another and we started sexting and sending pictures.

I haven’t felt this alive in years, I’ve felt so confident and happy and it’s been positively affecting other aspects of my life. I don’t just feel physically attractive again but also funny and intelligent, I’ve been able to contact old friends again because I feel like I’m worth something again.

We both knew what we were doing is wrong and neither of us ever thought we’d be capable of cheating until we met each other.

He decided to end things this morning, he said he wanted me to be happy and he wouldn’t be able to make me so since we agreed that we wouldn’t leave our partners and he was afraid we’d get to a point of no return. But I already feel like I’ve fallen in love with him.

It hurts so goddamn much, so so much and all I want to do is reach out to him for comfort but he’s the last person I should go to. His happiness and well-being are so important to me but I want to be with him so badly at the same time.

Is it possible to stay friends with him like he wanted? I told him I didn’t think I could and he’s stopped contacting me, but I want to talk to him so much. He’s such a precious friend and I don’t want to lose that especially since I’m one of three people he’s talked to about his trauma and I want to be there for him.

I’m a grown woman with a boyfriend going through my first heartbreak and I have no one to turn to other than the source of my heartbreak, what do I do.

Thanks for hearing me out,

Wanting What I Can’t Have

So, questions about affairs are always controversial ones, WWICH. There’s going to be a lot of discussion about the rightness or wrongness of it, whether simply sexting counts and the wisdom about having lied about your age when you met your boyfriend (and a lot of questions about someone who’s cool with dating somebody that much younger than him who also lied about her age).

But short of my loaning you a time machine, there’s nothing to be done about the past. Instead, we need to focus on your future”both in the immediate short term and the long term.

Starting with this: I’m not entirely sure why you were still with your boyfriend before you had this affair, and I’m really unsure why you’re still with him, or why you weren’t willing to leave him before the affair ended. While I’m firmly on the record that I don’t think that cheating is the worst thing that can happen in a relationship or that it’s necessarily a relationship extinction level event, this affair, should have been, if only for your own good.

If nothing else, this should be a wake-up call to just how badly things have gone with your partner.

I mean, the fact that you have no intimacy with your boyfriend at all and go for years without having sex should be enough of an indicator that this is relationship is already over. But just as importantly, your relationship with your boyfriend has so destroyed your self-esteem and self worth”never mind your being able to feel attractive and desirable”that you don’t feel like you can stay in contact with your old friends. That’s not a red flag, that’s the running of the goddamn bulls in Pamplona.

I’m not surprised that you fell for your co-worker. You’ve been starved for affection and physical and emotional intimacy for so long that his attention and desire was like water in the desert. Just feeling like somebody liked you was enough to cause you to bloom like a flower once more.

The problem, though, is that while the emotional intimacy and desire was what you needed, you were getting it from a source that was going to dry up eventually. You weren’t willing to leave your boyfriend and he, understandably, wasn’t willing to upend his entire family over this. Which, unfortunately, has left you in a state a little worse off than before. After all, it’s hard to mourn the loss of a relationship when you can’t let people know you were even in the relationship in the first place.

That makes it more difficult to heal and move forward. Not impossible”time heals all wounds and wounds all heels”but it does prolong the pain.

But there are a few things you can, and frankly should, do, WWICH.

The first is simple: you need to let go of this guy. While I’m generally a believer that it’s possible for people to be friends with their exes after a break-up, that requires time to let yourself heal and distance from the relationship and the break-up so you can get perspective and not be in the same headspace as you were when the relationship ended.

You are in no place to be friends with him. Certainly not now, possibly not for a long, long time. Not only are you in pain and still harbouring dreams of getting back together with your ex, but, honestly, I think you’re overestimating your feelings for him. I don’t doubt the intensity of them, but I think what you see as love is actually infatuation and the feeling of finally being desired and appreciated for the first time in years. When you’re dying of thirst, that first drink of water is going to be the most delicious thing you will have tasted in years.

With time and distance, I think you’ll understand that. But for now, you have to let this one go. You had a lovely dream, but dreams come to an end. And this one ended.

Next: reach out to your friends, especially the old friends you reconnected with. Are there any who you’re still close with, who you can count on to listen without judgement and to keep your secrets? They would be the people I would suggest turning to at this time.

In fact, I would strongly suggest that, even if you don’t discuss your affair with them, that you absolutely should stay in contact with them and rebuild the connection you had with them before you lost touch. You need your Team You right now, the people who love you, care for you and support you. You have an extreme deficit of love and emotional support and you desperately need that, even more than you need the attention and desire from your co-worker.

Just as importantly: I think you need to leave your boyfriend. I understand why you stay. It’s very hard to leave a relationship, even one that you need to leave, when you’ve been with them for over a decade. But the fact of the matter is that this relationship ended years ago; what’s left is the shuffling remains of a relationship that doesn’t know that it’s dead. Worse, the corpse of what you had with your boyfriend is dragging you down with it. Your relationship has been slowly eating away at your self-esteem, your confidence and your heart. You are miserable with him and it’s left you so empty that you don’t feel like you have a right to even connect with your friends.

The best thing you can do for yourself is to take this zombie relationship and put two in its brain so that it no longer has this hold on you.

It’s a terrifying prospect, I know. But it’s the short-term difficulty that will save your life in the long term.

Because here’s what you should take away from this affair: no matter how your relationship with your boyfriend has made you feel, you are still desirable. You can still find love. People still find you attractive, people still want to date you, people want you in their lives.

If you were to leave your boyfriend, I think you would discover that there’s a world of possibility waiting for you. A world where you can find the connection, the intimacy and, yes, the sex that you are lacking in your life right now. It’s a world that’s waiting for you to realise that you have far more to give, instead of wasting any more time with a relationship that’s choking the life out of you.

Having this emotional affair with a married co-worker may not have been the wisest decision you could ever make”¦ but it’s one that may end up finally changing your life for the better, if you just take this opportunity.

The dream of being with your co-worker is over, but now you can wake up to a better, brighter world. But it has to start with your letting go of the past”both this affair and this relationship that’s holding you back.

Good luck.

Hello Dr. NerdLove,

I’ve been reading your posts for almost 4 years now and I think the time for me to ask something has come.

First off, I’m a Venezuelan 19 year old man, about to turn 20 in May, so I understand I might be a bit young and probably over exaggerating things, but hear me out here. My life up until this point has been pretty similar to the usual geeks’, staying at home, playing video games, watching anime and generally just enjoying time with myself. However, after I became a teenager I started to get into fitness and in turn began to get unexpected attention from women.

The society I live in is pretty different from the others, criminal rates make people very cautious of who they hang out with and in turn makes getting to know people better way harder, the economic situation also doesn’t help since it prevents a lot of individuals from enjoying their real hobbies.

I’ve never been a super popular person for many reasons, my incursion into the dating world started as recently as 2018, since then I’ve had many opportunities with women that made me grow a lot as a person but it wasn’t long before I started to see a pattern in the women I was dating with. People come and go in Venezuela, the goal for any college student is to leave the country once they’re done with their degree and that’s OK, but because of this, they all also fear relationships and the commitment that goes with them, which is why I never got a chance at getting a girlfriend.

Was this everything though? No, it wasn’t enough of a reason, so I started to think about it more and more until I had my first real relationship. The girl I was with was the best, she was easily the best girl I’ve ever had in my life both in looks and mind and also the closest to what I was looking for in a girlfriend but there was a catch, she was extremely unstable. Her family was also not the best and ultimately it all fell apart in a pretty horrible way. What do all these girls have in common? Well, not only did they not want a relationship but they also weren’t compatible with me if you thought about it. Everything was always about “˜trying to make things work.’

Which brings me to my next point, I’ve never really dated anyone with a real connection to me, like a hobby we both really enjoyed or personality traits that really linked us together, I’ve never had that opportunity. I understood this and did what every geek has done since the dawn of time. I started looking for geek girls.

Fast forward to today, I am starting my second year of university and I’ve had no luck in this endeavour, my breakup happened at the end of 2019 and all the women I’ve been approached by since then have all been the same, even if I did end up liking some of them back.

It’s not even about getting them to like me, I actually don’t see any of them, I don’t know where to look, I don’t know where to go, dating apps don’t really work here and it’s not like the US where you can just hang out at gaming stores and talk to people or just get into online groups, I just don’t know where these women gather or where to start and these groups aren’t obvious at my university either.

I understand looking for a woman with certain interests doesn’t always bring you success but I want to try this. Having this in mind, what would you do?

How can I find a geek girl and get to know her with all these obstacles in my way?


Royally Screwed

First and foremost, RS: the fact someone likes the same video games or shows on Crunchyroll that you do doesn’t make them your soulmate. While having similar hobbies is a good start, it’s not going to bridge the rest of the gap. You want commonalities with the people you’re dating, but while hobbies and interests are a start, you need to be willing to get deeper than that. Shared goals or values are often more important, especially in the long term. Just because someone doesn’t currently share your interests doesn’t mean that they’re not compatible with you. Someone who’s open to trying your interests or who can at least relate to the fact that you love the things you enjoy can be a better long-term partner than somebody who may not be a great match for you personality-wise but at least they also dig Bloodborne.

So finding someone who you mesh with on that level may be not just an equally good match, but one that’s easier to find under your current circumstances.

(And needless to say: the things that somebody consumes, whether TV, music or games, aren’t a substitute for a personality.)

But let’s talk about where you can find a single geek woman in this day and age.

You need to think like a hunter. If you’ll pardon an inelegant metaphor: if you’re a hunter looking for deer, you want to find the places where the deer gather. If you’re looking for women with geeky interests, then you need to find where those women hang out, either in person or online. And while I realise that Venezuela’s culture and social mores aren’t exactly the same as America’s, I find it difficult to believe that there are no women, especially college students and women in their late teens and 20s, who aren’t interested in geeky subjects.

The most obvious place to start looking would be to check the extracurricular activities attached to your university. Things like an anime club or anything related to scifi, fantasy, tabletop games or comics would be the first place to start making inquiries. You may also find unofficial groups, like people who get together regularly to watch Picard, for example.

It’s important, however, to not get tunnel vision and focus exclusively on the activities you think of as geeky. Instead, you may want to bankshot it by finding places where women who have geeky interests tend to gather that aren’t overtly geeky in and of themselves. You aren’t as likely to find large numbers of women who are involved in competitive esports, for example. You are, however, more likely to find women who have geeky interests, in, say textile arts or creative writing programs. Women who are active in the fanfic community might be more likely to end up in literature or creative writing. You may also find them in the art department, where folks who do fan art or cosplay might be more likely to gather. Alternately, you may find them in the history department or poli-sci.

You also should check online. Local forums, discussion groups, even Facebook groups might be a resource for meeting women of a geekier persuasion in your area. But again: don’t just focus on the things that YOU think of as being geeky. It may be that you’ll need to broaden your horizons a bit. Critical Role, The Adventure Zone and other RPG real-play shows on Twitch and YouTube have sizable contingents of female fans; finding the fan groups in your area might be a place where you can meet fellow geeks or possibly even find a new obsession of your own.

But as I said, sometimes the key isn’t to find someone who’s already a geek. Occasionally you need to find someone who you’re compatible with who may not be a geek but is at least geek curious. Introducing her to some of the things you’re into might be the way to find someone who could share your interests, even if they don’t already.

Just do yourself a favour and be as open to trying some of her interests too. Fair is fair, after all. If you’re going to hope to get someone into your interests, it’s only reasonable to give hers a try as well.

Good luck.

Did you get a date while on the job? Have you broken up with someone who you were dating in secret? Share your story in the comments below and we’ll be back with more of your questions in two weeks.

Ask Dr. NerdLove is Kotaku‘s bi-weekly dating column, hosted by the one and only Harris O’Malley, AKA Dr. NerdLove. Got a question you’d like answered? Write and put “Kotaku” in the subject line.

Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove YouTube channel. His new dating guide New Game+: The Geek’s Guide to Love, Sex and Dating is out now from Amazon, iTunes and everywhere fine books are sold. 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.

More Dr. NerdLove


  • As proven time and time again by these useless articles, your ‘advice’ is a joke and you’re an embarrassment to your profession. Many times in the past your advice has been downright sociopathic and damaging.

    • I dunno man. It’s advice. He’s not a doctor. It’s stated repeatedly. And I’ve seen him recommend seekun professional help countless times.

      I don’t agree with every piece of advice he gives, but there’s always many different approaches one could take (or advise) in any situation.

      There’s no absolute law book of rules & regulations for this stuff. I think he generally tries to look at the situation from the perspective of empowering the letter writer. Or at least to look at using their anecdotal experience as a lesson, something productive to grow from – and inform the reader and original correspondent.

      So yeah, I can understand why some people would vehemently disagree with his advice. There’s many relationship advice Q&As online, with many different tones & approaches. I can only assume people direct their requests for advice to the ones they read or a familiar with, as many “Hi longtime reader first time writer” letters begin.

      And the not being a Doctor part is strange, because most every single counsellor, when presented with a relationship problem , one on one – will focus generally on achieving a result focused on empowering and improving the overall happiness of the client/patient, rather than their (non patient) partner. Much like DN does.

      So yeah, it’s totally reasonable for you to disagree with his advice vehemently if that’s where you’re at. I just wanted to let you know it’s not universal.

    • I’d be REALLY curious to know what parts of that very extensive advice you take issue with.

  • And yeah, I’ve seen plenty of shockers from him, I’ve been reading as long as he’s been here on Kotaku. But this is light entertainment media, not a peer approved journal. It’s hardly presented as such.

    Context wise, this is up there sharing server space with “Top 10 favourite game lists” , “Best xyz released in year abc ” & “My favourite FF numbered title is …” subjective opinion/informing readers articles, that will infuriate some (FFVIII all the way! No, Youre wrong!), delight others, but generally exist to share an opinion or perspective with the broader readership.

    If you strongly disagree with advice he gives, job done I guess.

Show more comments

Comments are closed.

Log in to comment on this story!