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

DEAR 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 bulls--t 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.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I’ve (24/M) been interested in “Mary-Anne” (26/F) for a while now, ever since she was introduced to my circle of friends by a mutual. She’s practically like someone built my perfect woman in a lab. She’s beautiful, intelligent, and funny, we’re both gamers and love D&D and stuff like Critical Role. I could listen to her talk for hours because she’s got wild ideas and theories about stuff and even if I don’t agree or think she’s wrong, they’re at least fascinating or hilarious.

The problem is, I’m having trouble figuring out if she’s interested in me too. We got along great from the first time we met, we DM each other often outside of the group chat my friends and I have, we’ve hung out in groups and gone to events together, so I know she at least likes me a little. I just don’t know HOW.

The problem is that I can’t seem to read her signals. Sometimes I think she’s flirting with me, but other times she’s just friendly. For example, she’ll laugh at my jokes and touch my arm, but then she’ll mention another guy she’s interested in or say that we’re just friends.

I’ve tried to initiate one-on-one time with her, but I always have to chase her down. I’m usually the one who starts the conversation (she does occasionally message me, first), and she always seems to be busy or unavailable. When we do hang out, it’s because we’re at the same group things together. We’ll spend time talking when it’s just us at them, so I don’t know what would be different about it just being her and me, not her and me and four or five other people. What’s the difference between coming outside to keep talking to me when I need to smoke and going out, just us, if everyone else is in a different room or different part of the house? I don’t know if she’s intentionally avoiding being alone with me, or if it’s just a coincidence.

I’m starting to feel frustrated because I don’t know if she’s interested in me romantically or if I’m just stuck in the friend zone. I don’t want to ruin our friendship by making a move if she’s not interested, but I also don’t want to miss my chance.

Why is she cool with hanging out with me alone when we’re out with other people, but doesn’t want to see me when it’s just us?

Thank you for your help.

Sincerely,

Doesn’t See The Difference

DEAR DOESN’T SEE THE DIFFERENCE: This one’s easy, DSTD, but I’m afraid it’s not what you want to hear. She likes you, but not the way you hope.

She knows you’re interested in her as more than a friend. She’s also almost certainly hoping that you’re going to pick up on the “not interested in you as a lover” vibe, so she doesn’t have to make things awkward by turning you down directly.

So here’s the thing: I tell people all the time not to assume too much based on any one point of data. If you’re having a hard time trying to get someone to spend time with you because they’re always busy or always have a scheduling conflict, that doesn’t mean they’re trying to avoid you. People can be stupidly busy and not have the time or energy to spend time with people, even people they really would like to see. Similarly, not being the first to initiate a message or to DM someone doesn’t mean that they’re not into you; sometimes they’re afraid to message first because they worry about bothering you. Other times, that’s just the dynamic of how your friendship works.

But to paraphrase the sage: one sign of potential disinterest is happenstance. Two is coincidence. Three is enemy acti^H^H^H a message.

Case in point: she’s cool with being alone with you at parties or group get togethers, but doesn’t seem interested in doing stuff with you, solo. The difference, in the words of It’s Always Sunny in Philadelphia, is “the implication.”

That is: what is the unspoken, hidden meaning or subtext of the interaction, you’re having?

If, for example, you’re all at a friend’s house to watch Critical Role’s Twitch stream – to pull a random example – and she comes outside with you to continue the conversation you were having while you take a smoke break, there’s going to be a different subtext to the interaction than if you two were out, just the two of you.

The fact that this is a group event, something you’re both attending specifically because you’re hanging out with mutual friends in the same space, means that this isn’t going to have the same subtext as the two of you going out to do something together. She’s willing to hang out with you individually, at group events, because the implication isn’t romantic or sexual. She likes talking to you and wants to keep the conversation going, but there’s always that subtext of “this is a friends group event” to it. In all likelihood, she’s relying on that subtext to discourage you from seeing it as an opportunity to be romantic. Since you clearly are hesitant to actually try to say anything where other people may overhear or interrupt, this means that you’re less likely to say the unspoken thing she knows is there and is trying to avoid.

If it were just the two of you, from start to finish, with the intention of it just being the two of you out together, doing stuff… well, you’re clearly bringing the implication that this is a date-like activity. I suspect that if you weren’t giving of the “I really want to date you” vibes, then she’d be more inclined to hang out as friends. As long as the implication that this is ­– or could be – a date, then she’s going to have reasons why she can’t make it.

In other words, while any one thing she’s doing could be an unfortunate coincidence, putting it all together makes it pretty clear that she’s giving you a soft “no”; that is, the subtext to her action is that she is cool with being your friend, but doesn’t want to have to make things overt. She likes you… but she’s a little worried about how you’ll take it if she turns the subtext into text.

And honestly… it’s hard to blame her. Almost every woman out there can tell you about a guy she thought of as just a friend who tried to pull Schrodinger’s Date on her, where they were both on and not on a date, depending on how she reacted. And just as many can tell you: a lot of guys they thought of as friends reacted badly when they were turned down directly. So the odds are good that she’s had this happen to her before, and she’s trying to avoid it this time around with you.

Are you likely to turn into a hate-fueled rage monster by getting a direct “no” instead of a soft, socially acceptable rejection that doesn’t underline a lack of romantic interest? Probably not. But too many women – likely including Mary-Anne – have had it happen to them. So rather than risking a negative response, having a way of waving you off that doesn’t directly hit you in the ego feels like the safer choice.

I suspect you already know this; you just don’t want it to be true. You’re hoping for a different answer, which is why you’re reaching out to me instead. You want reasons to hold onto hope instead of letting go of this particular crush. Trust me: I have been there, done that and wrote the cringy LiveJournal posts about it.

It sucks, I know. But this is one of those times that you have to remember that having a crush on someone doesn’t mean that they’re going to be the last person you ever feel like this for, or that giving up on making that crush come to fruition is a betrayal of your sense of self.

If you genuinely enjoy spending time with her, then I think the best thing you can do is accept her friendship on the terms she’s offering and let this awkward crush fade. And while I know it’s hard – especially the way you feel right now – don’t take this as a judgement on you as a person.

You aren’t going to be able to fully appreciate this now, but hopefully this will be a comfort to you later, when the sting isn’t so fresh: just because someone doesn’t like you the way you want doesn’t mean they don’t like you at all or the best that they can.

She likes you, DSTD. Just not the way you hoped. Be her friend instead. Friendship isn’t second place to love; it’s a reward in its own right.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I’m in my late 20s and am living a life I really enjoy. I work an interesting job and regularly go to cool movies, bookstores, hiking trails, concerts, and comedy shows, and the like.

The caveat is that I do all these things alone. I hang out with friends sometimes but I don’t see them often, as they are rarely available (and if I only went to places when my friends were available, I’d never leave my apartment).

I bring this up because I think my lack of regular social interaction makes me ill-equipped to date. I’ve never had a girlfriend in my life and I can’t help but feel I’ve missed out.

The few women I’ve had sex with phased me out as soon as we hooked up. The women I “cold approach” or outright ask out always react uncomfortably (I could be misreading that but either way, I don’t get a date this way. It probably doesn’t help that I look odd being out at places alone.). Other women I meet are only interested in being friends, which is totally fine, but then they become like my other friends who ghost me and rarely make time to hang out.

I relied on dating apps for some time and met some great women that way. However, every woman I dated said the same thing to me after one date: they didn’t want to go on a second date with me because they “didn’t feel a romantic connection” (it’s to the point I suspect they’re just reciting the same script).

At first, I thought my dating inexperience was my issue so I sought to learn from mistakes. I started dressing better, I picked more interesting dates with women I met, I made an effort to engage in better conversations where I really listened to them, and I even proved I wasn’t afraid to make a move. Evidently, none of that mattered because I still got the “I didn’t feel a romantic connection”, even with women I thought I had a lot in common with.

For now, I’m off the apps and prioritizing other areas of my life above dating.

Yet, it still bothers me that I may never have a girlfriend because me having one would apparently break the Laws of Nature. I think there’s just something about me that at best, makes people only want to handle limited amounts of, and at worst, makes them want to outright avoid me. No one can tell me what exactly that is, so I’m left guessing.

If I really felt I was hopeless, I wouldn’t be writing to you. On some level, I think I just need to fix my approach or be more patient. Then things might happen!

However, I don’t think that’s a guarantee and really wonder if maybe I have to accept I’ll never be with anyone.

Your thoughts appreciated!

Sincerely,

Nothing Wrong with Being a Loner

DEAR NOTHING WRONG WITH BEING A LONER: Here’s the thing: without following you around and documenting your dates like a romance-focused David Attenborough, it’s hard to say specifically what you’re doing wrong. However, I think there’s enough in your letter to give an idea about what’s going on.

There’re a lot of reasons why someone – or several someones – may not feel chemistry with a person. Sometimes it’s just a matter of incompatibility – there’s something integral to one or both of them that doesn’t mesh in the way that’s necessary for attraction to bloom. But other times, it’s because at least one person or both people aren’t actually creating that spark and are, instead, hoping it just happens.

This is why I think you’re correct, NWBAL: I think your generally solitary lifestyle is having a direct effect on your trying to meet and date women. I’m a big believer that one’s love life is a reflection of your holistic self; many times, any issues you have with regards to love, sex and dating are directly reflected in other areas of your life.

You wouldn’t think that this would be some grand revelation. However, a lot of people have a tendency to think that their love life – from who they meet, who they attract, who they’re attracted to and how people respond to them – are entirely separate from the rest of their lives. So you get people who never leave the house, never talk or interact with other people and have very little going on in their lives outside of work, who’re shocked, shocked, that they aren’t living the playboy lifestyle with hot and cold running sex at all times.

This isn’t to say that everyone needs to be as active as a social butterfly on a cocaine binge in order to date. It does, however, mean that the social skills you bring to dating are the same social skills you use in your daily life; the only difference is the intent behind them and how you put them into practice.

Please note very carefully that I say skills. We don’t call them “social skills” because alliteration in English is especially pleasing to the ear. We call them social skills because they’re just that: skills. They are an ability that you improve with deliberate practice.

That also means that if you don’t practice them, they tend to atrophy.

Now, I mention this because people often have a mistaken idea of what people mean when they talk about “chemistry” or “that spark” that they feel with some people, but not others.

The term “chemistry” is a bit misleading… but not entirely inaccurate. When we talk about “chemistry”, we’re really talking about an emotional state of attraction and interest, not necessarily something involving Bunsen burners, Erlenmeyer flasks and weird colored liquids bubbling and smoking all over the place. If someone isn’t necessarily feeling that chemistry or that spark with someone, they’re saying that they aren’t feeling romantic or sexual attraction to them, rather than “their pheromones aren’t doing it for me.” In many ways, we treat this as a binary – either you feel it or you don’t. If fate hasn’t intervened to put two crazily compatible people together on this date, then there’s just nothing to do but shrug and move on.

However, there is a chemical aspect to attraction, on top of the emotional. Love isn’t just a feeling, it’s oxytocin and dopamine hitting the pleasure centers of our brain. Part of why, for example, couples get weird and schmoopy about one another in the early days of their relationship, it’s in no small part because they’re literally getting high from being around each other. The oxytocin and dopamine and all those other feel-good chemicals are giving them an all-over love buzz, as it were.

But chemistry – metaphorical or literal – between two people doesn’t just “happen” by chance. It’s not a matter of luck or destiny… it’s also something people can create, if they put their mind to it.

What are some of the things that help create those chemicals? Well, amongst other things: physical touch, laughter and good conversation. All things that are well within your capabilities… as long as you put them into practice in the right way, and with the right mindset. You want to pay attention to what feelings you’re trying to generate and how, not just leaving it up to chance.

Building chemistry with another person is a type of social skill; you’re focusing on creating warm, positive feelings in them, feelings that they will attribute to being in your presence. The more that you make people feel good when you’re around, the more that they will subconsciously prioritize their relationship with you – the provider of those good feels – over someone else. This is what’s known as The Reward Theory of Attraction.

The reason I bring all of this up is because you spend a lot of time rolling solo. In and of itself, this isn’t a bad thing. However, if it means that you’re not regularly hanging out with other people and putting those social skills to use – maintaining friendships, making new ones, and so forth – then there’s every likelihood that you’re not keeping those particular skills active. Those skills – the ones you use to make new friends and stay connected with current ones – are the same skills you use to connect with your dates and build attraction; you just implement them in a slightly different manner.

The tell, here, is that you’re having some success with meeting women on dating apps, but less so when you meet people in person, and the women you go on the dates with are bouncing after you get together. While this isn’t unusual in and of itself – I’ve written extensively about how dating apps give a lot of false positives – this level of consistent response tells me that it’s what you’re doing on these dates that’s causing the issue.

It’s good that you’re listening and showing that you’re confident enough to make a move, and it’s good that you’re trying to plan more interesting or unusual dates. That’s a good start. As I said, you’re doing a lot of the right things. However, while you’re on dates, you want to be mindful of the kinds of feelings you’re creating. When we’re talking about that spark of romance, we’re talking about a mix of both good feelings and excitement, not just a mild, pleasant sensation. So if your dates are mostly feeling decent-but-not-terribly-memorable, then you’re not going to generate that spark of interest.

This is part of why flirting, for example, is important. Flirting is both signaling interest, but also creating a feeling of fun and excitement. It’s about building that sense of interest and tension before providing a release.

The same is true of humor. Women say they love a man who can make them laugh for a reason, and one of those reasons is that they demonstrate they know how to make them feel good. Humor frequently works on the same sort of “build-tension-and-release” mechanism as flirting; this is why banter or teasing can be a powerful flirting technique.

Creating feelings of similarity and connection – the sort of excitement of “my god you GET me!” – are another example. Think of the times you met someone and the thrill of connecting with them over having a similar background, taking the same major in college, loving the same movies and so on. Finding those points of commonality, especially the deeper points of similarity, like shared values or backgrounds plays an important role when it comes to creating chemistry.

So, if you’re having conversations where you’re just being a good listener, but you’re not engaging with them, sharing your thoughts as well, relating to what they say and connecting with them on a personal level? That’s going to lead to people not feeing the spark. So if your conversations aren’t mix both making them feel understood and appreciated and being engaging with your insights or experiences, then you’re going to be working with a handicap.

And focusing on those good feelings is part of what makes someone sexy. Part of why some folks have that je ne se quois is because they’re very in tune with their senses and their own body, and with others. Rege-Jean Page made using a spoon seem positively obscene with the level of sensuality he brought to it… and left women everywhere wanting to be that spoon in the worst way. This is one reason why guys who can dance are sexy as hell; they demonstrate a level of awareness of their body and the use of it, their appreciation of the sensual pleasure of music and movement, their level of control, and so on.

Now, I fully acknowledge that it’s easy to say this, but a harder thing to do. One of the tricks with improving your social skills is that you have to put them into practice, and that means practicing with other people. So part of what will help you do better on dates is to work on getting better with people in general. If you can make a friend, you can find a lover. If you can talk to a stranger and build a connection with them, you can get a date.

So my advice to you is to focus and find opportunities to be more social in general, whether this means hanging out more with your co-workers, making small talk with people during the day or taking more time to enjoy your hobbies with other like-minded people. Put those social muscles to work in platonic areas and you’ll find that your non-platonic ventures will show improvement, too.

And yeah, there will be some awkwardness as you do this. You’re trying to work muscles that haven’t been put to full use in a while and you’re going to be trying to do things that may feel unusual or strange at first, and you’ll likely feel a little cringe at points. Push through that; this is just the pain of the unfamiliar and the new. The more you practice at it, the more you’ll find what does and doesn’t work for you.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com