What’s The Best Way to Ask A Stranger Out On A Date?

Estimated reading time: 16 minutes

Dear Dr. NerdLove:

I’m a university student that discovered your blog a few days ago and I wanted to ask you a question. There’s this cute girl that has recently started to work at a local bookstore that I sometimes go to and I wanted to get to know her and if possible exchange numbers or Instagrams later on. I do not want to distract her from her work, as probably the last thing she wants is an annoying, although good looking, stranger not letting her do her job. I worry as well about putting her on a situation where she might have problems with her supervisor or something similar.

I had thought about trying some short friendly conversations with her asking her about her work and books she might like or that she could recommend. And if things progress well after some conversations, I was thinking of giving her my number/Instagram on a note instead of asking about hers, in order to take some pressure off her. 

I know that falling for someone that works at a store is not an ideal situation, actually is probably far from it, but I thought that maybe you could give me some tips! And if you want you can take advantage of this question and explain the do’s and don’t’s of asking out someone that works at retail or a store.

Sorry if there were any grammar mistakes, English is my second language.

Thank you and I hope to hear from you soon,

A Spanish Bookdragon

So, this is a question I’ve been getting… pretty much from when I started this column, SB. I only mention this because, having done this for as long as I have (and we will pointedly NOT be thinking about how long that’s been, because I feel old enough as it is…), one of the things I’ve noticed is that there are two questions embedded in one.

The surface question is, frankly, fairly simple. There is no “best” way to ask someone on a date; the best way is the one that worked for you. As a rule of thumb, matching the way you pursue a date with someone to your overall personality is the way to go, as long as it actually gets you the results you want. If you find that hiring a plane to fly a banner reading “Hey, Agatha, want to get drinks next week? – Nathan” over their neighborhood gets you a date then clearly that worked for you, and also you (and Agatha) clearly don’t care if all of her neighbors know her business.

So if you want to leave a note with your name and contact info on it for her, rather than asking her directly you can certainly do that.

But the second question – and the one I suspect is buried in your letter – is “what is a way to ask her out that has a chance of actually working?” And this is a very different beast entirely.

Here’s the thing about flirting with people in service industries, especially while they’re on the job: it’s usually a bad idea, for a number of reasons.

To start with: someone who’s in a front-facing, customer service position, whether they’re a server at a restaurant, a bartender, or a store employee spends a fairly significant portion of their day dealing with folks who think of them as meat robots who are there to accede to their wishes, not as actual people. This means that a lot of their day is filled with people who are yelling at them, making unreasonable requests and – especially if they’re femme-presenting and conventionally attractive – getting hit on relentlessly.

Sometimes this can work to their advantage, to a limited extent. If they work for tips – as servers, bartenders and dancers do – then they know that being flirtatiously friendly means that customers will likely tip more. They also know that having friendly interactions with people means that a percentage of those people are likely to come back to see them, ideally eventually becoming regulars. So there’s a distinct incentive to be flirty and seemingly available without ever actually doing something; the long tease, as it were.

(Admittedly, that framing is a bit unfair because it implies a level of dishonesty and manipulation rather than a result of capitalism incentivizing not paying a living wage and doing what you need to do to make money, but functionally that’s what’s happening.)

Other times though, the primary incentive is “don’t lose this job”. Especially for people who work dealing directly with customers. So the bookstore employee needs to maintain a certain level of “polite friendliness”, even in the face of people being rude or dismissive or overly aggressive. Especially in jobs where their bosses and managers are monitoring their “productivity” with various bullshit metrics.

Now, I bring this up because these concerns are going to directly affect your interactions with your crush. She’s going to be incentivized to be friendly with you when you talk, to not piss you off by turning you down (in case you go complain to her manager and she works in a place where management doesn’t have their employee’s backs) and that talking with you for too long or too often could potentially jeopardize her job.

So you’re going to be dealing with someone who likely gets hit on regularly, who has to at least pretend to be friendly and interested in the name of customer service, and who may well get penalized for talking with you for longer than the customer/bookseller interaction calls for. Plus you’re doing it at a place and time when most people aren’t necessarily open to meeting potential dates and the social context doesn’t support that sort of behavior.

Does this mean you can’t talk to her? No… but it does mean that you’re going to be dealing with levels of difficulty that you wouldn’t be experiencing in other circumstances. You’ll metaphorically sailing this particular ship into some serious headwinds and hoping that it actually gets you somewhere.

And all of this is before we get to the basic fact that what you know about her is… she’s a cute woman who works in a book store. Which may be your exact flavor of yum… but that’s literally all you know about her, and she knows even less about you. You don’t know if… I dunno, if she supports Manchester United over Spanish football teams and she doesn’t know if you’re a serial killer who looks at the Netflix show “You” as an aspirational guide.

So if you do decide to pursue this, you’re going to need to be ready to look at this as something that’s going to take a while to develop – likely weeks, depending on how frequently you can reasonably go to the store.

(And I say this as someone who’s on reasonably good terms at some of the stores or restaurants I visit regularly – enough to talk about major life stuff with the employees I know – but that was something that was built over months, usually going on a weekly basis.)

Your general idea – make small talk while you’re there as a customer – is a decent one. However, you’re going to be dealing with the fact that these are likely going to be short conversations because of logistics, and it may take a while before you have built up enough trust and connection to get to more personal, less work-oriented topics.

This can be done, but it definitely means that for it to work well, you’ll need to be very socially well-calibrated and prioritize her comfort and need to work over your interest in getting to the point where you can ask her out. It also means you’ll need to handle any flirting or demonstration of interest with care. Many women can tell you stories of customers whose obvious interest made it awkward for everyone, especially for the employee.

Similarly, you need to be able to thread the needle of being not only able to ask someone out on a date, but being able to stick the landing with grace and finesse if/when she turns you down. The last thing you want is for her to feel uncomfortable when she sees you’re in the shop or for you to feel like you can’t go back there because the vibe is so awkward now. Especially if this is a bookstore you actually like going to.

Now I realize I made this sound like the emotional equivalent of trying to defuse a nuclear bomb with a loud beeping countdown and your least favorite gym teacher breathing down the back of your neck while you do it. It’s not that dire or complex a situation, but it is one that has a lot of challenges and drawbacks. If you know, honestly, that you’re good at threading this needle… well, you can certainly try. I think you’ll have a better result if you let this be a “I occasionally chat and lightly flirt with this person when I’m there, but I’m actively pursuing other potential relationships” scenario, where you’re willing to let it simmer over time? That might – and I stress might – work out eventually. But if you know that you’re prone to discomfort and awkward feelings around rejection or you aren’t willing to let this put the “slow” in “slow burn”? You may be better off looking for people in more social venues.

Or you could focus on chatting up a cute customer instead – again, provided you know that you’re calibrated well enough that you don’t make them uncomfortable. That’s worked out for me more often than chatting up the employees.   

Good luck.

Dear Dr. NerdLove, I’m a 32 year old woman who has been with my boyfriend (“David”, 35) for a little over a year. We’ve always had a great connection and I thought we were on the same page about our relationship.

However, recently my boyfriend dropped a bombshell on me. He told me that he’s polyamorous and wants to have an open relationship. I was completely caught off guard and I don’t know how to feel about it.

On the one hand, I want to support my boyfriend, especially if this is genuinely part of who he is. But on the other hand, I’m struggling with feelings of inadequacy and fear of losing him.

I can’t help but wonder if this means that he’s not satisfied with our relationship or if he doesn’t love me enough. I feel like I’m not enough for him and that he needs more than what I can offer. I also worry about how this will affect our connection and whether we can maintain the closeness we currently have.

I tried to be understanding and supportive of his feelings, and I understand that everyone has different needs when it comes to relationships. However, the more I think about it, the more anxious and insecure I feel.

I can’t shake the feeling that my boyfriend wants something more than what I can give him. I worry that he’s already cheating on me or has someone else in mind, even though he’s never given me any reason to mistrust him. I know that it’s irrational, he’s never even been ten minutes late without texting me first, but I can’t get that fear out of my head.

I know he’s attracted to other people, and I’m afraid that I won’t be able to meet his needs and keep him interested.

To make matters worse, I don’t have any experience with polyamory or open relationships. I don’t know how they work, what the rules are, or how to navigate the emotions that come with it. I’m afraid of making a mistake or doing something wrong that could hurt my boyfriend or our relationship.

I’ve tried to talk to my boyfriend about my concerns, but I’m not sure I’m explaining my worries clearly and I don’t know what I’d need from him so he can reassure me. He tells me that he loves me and wants to be with me, but I’m having a hard time believing him. I’m afraid that if I agree to an open relationship, I’ll be setting myself up for heartbreak.

Overall, I’m feeling lost and unsure about what to do. How can I handle this request from my boyfriend and still feel secure in our relationship? How can I learn more about polyamory and open relationships and decide if it’s something I want to explore? Any advice you can offer would be greatly appreciated.

Thank you for your time,

Poly-blindsided

This is going to sound a bit weird, but… I appreciate your telling me that these are more about your issues regarding non-monogamy, rather than your boyfriend has been acting sus or that this is a “better to beg forgiveness” situation, where your boyfriend is trying to retroactively justify doing something shitty. That makes a big difference in the way to approach this issue.

In an ideal world, if this were something your boyfriend already knew about himself, this would have been a conversation you would have had much earlier – preferably during the Defining The Relationship talk. In my opinion, if someone knows themselves to be non-monogamous or polyamorous (and doesn’t currently have other partners), then it’s best to establish that at a certain point in the future that you’ll discuss the possibility opening the relationship up. Until that point, it’s best the relationship as monogamous so that you can establish that baseline of trust, openness and communication that can make it easier to talk about it without feeling like you’re being asked to agree to letting your partner bang someone else.

Unfortunately, your boyfriend handled the start of this conversation in a less than ideal way. From the sound of things, it sounds more like it was good intentions handled poorly, rather than a “I am altering the terms of our arrangement; pray that I don’t alter them further.” scenario. It could be that he thought that a year together was enough for you to be able to trust his feelings for you and didn’t realize that this would come screaming out of the clear blue sky at you. Or it could be that he was less than smooth at trying to bring up the topic, in part because he only just discovered this truth about himself. Most poly or ethically non-monogamous people tend to start out in monogamous relationships and then discover that it’s not a good fit for them.

But now that it’s out there, the thing to do is for the two of you to sit down and have a series of conversations about this. Notice very carefully that I said “conversations” – as in, plural. This isn’t something that’s going to get sorted out in one marathon Awkward Conversation; it’s something you’re going to want to discuss multiple times, especially since different aspects will crop up for you on different occasions.

The first thing I would suggest is for you two to sit down and talk about your immediate fears and concerns. And to be clear: these are reasonable concerns and worries. They are things that should be talked about, if only so he understand that you have them and he can hopefully help reassure you.

You’re worried that you’re not enough for him and what that means. That’s legitimate. You know that he’s attracted to other people. That’s legitimate too. Now, this is going to be the hard part for you to hear: no, you aren’t going to be everything he wants, and he’s always going to be attracted to other people. That’s not because there’s something wrong with you or your relationship, that’s just the condition of being human. I’m sure if you stop and examine things, you’ll realize that this is true of you, too – you’re attracted to other people, and you have wants and needs that your boyfriend can’t – not won’t – meet.

We can’t be all things to our partners; every relationship is one of compromise, and we can’t fulfill every desire or need they have or want. We pick and choose partners based on what we get from them being so good that we’re ok with not having the rest.

But at the same time, being polyamorous – assuming you and he are using the term correctly and not as a synonym for non-monogamy – means recognizing that love and attraction isn’t a zero-sum game. His being attracted to somebody else or having feelings for them doesn’t take away from his feelings from you. It’s very much a “yes, and” situation, not “instead of”.

Talking this through as part of the initial conversation may help ease your immediate worries and fears. Understanding that it’s not that he’s dissatisfied with you, doesn’t want to leave you and that it’s not that you’ve done anything wrong may help make the next conversation easier to handle. If he can reassure you – and you can let yourself be reassured – then you two can move on to continue talking. The next conversation would likely be talking about what this would mean for your relationship, how it would work for both of you, what it would look like, and so on. Then the conversation after that would be about how to handle complex feelings, managing feelings of jealousy or inadequacy, if you go through with it, while the one after that might be about how you would go about handling the logistics of managing an open or poly relationship.

However, between the first and second conversations – assuming that you don’t hit a hard “no, absolutely not” – I would recommend doing your research. Like you said: part of what’s making this hard for you is that you have no idea how it might work. Getting more information and a theoretical model to follow may help make things easier. Part of what makes this so terrifying for you is the sheer, vast emptiness of what to expect or what it all means. The unknown is always worse than the known, even when the known is unpleasant; at least with the known, you have concrete information, instead of a deeply uncomfortable space where everything could be possible and each worst-case scenario is even more soul-wrenching than the last.

Fortunately, there’re a number of books that I think are worth your time. My recommendation is that you start with Opening Up by Tristan Taormino, Building Open Relationships by Dr. Liz Powell (who, full disclosure, is a friend of mine and I’ve worked with them before) and Mating In Captivity by Esther Perel. The first two will help demystify the ins and outs of ethical non-monogamy and give you a framework to at least hang your questions and concerns on, while Esther Perel’s book is a wonderful discussion about human sexuality and relationships and the way our concepts about love, fidelity and monogamy have changed over time.

Now with all that being said: I want to emphasize that it’s absolutely ok if you have these conversations and do this reading and you still can’t get there. Non-monogamy isn’t for everyone and polyamory in general is like relationships on steroids; it requires incredible trust, free and open conversations and top-notch time management skills. There’s a reason why the most important member of a polycule is the shared Google Calendar, after all.

I also want to be clear that while being open or poly has its challenges and it’s fair to worry that opening up the relationship may lead to his leaving you, not being poly or staying monogamous won’t make your relationship break-up proof, either. We hear about failed poly or open relationships frequently, sure, but they don’t fail with a different frequency than closed ones. Nor, for that matter, do we consider that a closed relationship failing means that all monogamous relationships are doomed to failure, the way folks often do about poly and open ones.

So, in the name of being honest with you: you can do everything right – whichever way you go with this – and your relationship can still end with a break up. That’s just life. As the man said: it’s possible to commit no errors and still lose. But if you love and trust your boyfriend, and this isn’t an immediate “no, no way, nuh huh, no chance in hell” scenario – and it’s absolutely ok if it is – then the two of you should at least start the conversation and do the research. That way, at least, you can make your decision, for or against, with actual knowledge, rather than relying on anxieties or fears that may be more fear of the unknown or the imagined, rather than reality.

I hope this works out for you, whichever way it goes. Write back and let us know how it went.

Good luck.