DEAR DR. NERDLOVE: I’m a single female in her mid-20s and I went to a new dentist, who might be in his late-20s/early-30s, for an appointment the other day. He was extremely nice and very conversational. At first I thought he was just being nice (or indirectly flirting with his assistant – who is also young looking and beautiful).

But then he started asking me about food and restaurants, things I like, how long I plan to live in our state.

Then I saw he didn’t have a ring (which I know isn’t always a clue, but I used it) and so I started wondering, “is there more to his nice-ness?”

What are your thoughts? Was he being professional and nice to his new patient? Was he flirting with me and I have to make the move since it is his place of employment? Was he doing it to be nice around his assistant? Or something else I’m not seeing?

Thank you!

– Completely Confused

DEAR COMPLETELY CONFUSED: So this is an easy one, CC: he’s being nice.

Know how I know? Because he’s your dentist. You’re his patient. That means you are legally, ethically and professionally off-limits. It is literally against the rules for him to date or have sexual contact with his patients. Breaking that rule gets his medical license suspended, sanctioned by the ethics board and possibly thrown in jail. There was, in fact, a dentist in Ontario who was put on the sex-offender registry because of a sexual relationship he had with his patient.

His patient, for the record, was his wife.

So no. For many reasons, he was not flirting with you. And if he was flirting with you? Well… then he’s not likely to be your dentist for long. Or anyone’s, really.

(Oddly, this isn’t even the first is “is my dentist flirting with me” letter I’ve received. Did Shonda Rhimes create a show about sexy dentists that I missed?)

Now with that out of the way, let’s talk about the difference between flirting and being nice. This can be a tricky thing to suss out because… well, sometimes the answer to “are they flirting or are they being nice” is “yes”. There are a lot of reasons why somebody will flirt with customers and clients. Most of them come down to money.

Lots of folks in the service industry — especially people who work for tips or commissions — have a financial incentive to flirt. Most people in service industry jobs, especially ones like bartending, waiting tables, the shot girls at bars, even dancers at strip clubs, live and die by their tips. Anything that ups the likelihood of getting a decent tip — which can range from giving a mint with the check or putting a smiley-face and “thank you!” in the bill — can make the difference between being able to pay the rent that month or having to decide which meals they can skip so they don’t get evicted.

It’s also true that people — mostly, but not exclusively men — will spend more money if somebody flirts with them. Men are especially prone to this; it appeals to their ego and encourages them to act out. There are always guys who will want to impress women with how much money they can afford to throw around. This can result in them buying more — which increases the total tab and, theoretically, the tip — so they can show that they’re a big-shot.

There’s also the guy who thinks that tipping well will make him stand out and endear him to the server.

(It will, but not necessarily in the way that he hopes.)

And of course, there’s the gross variant of this who thinks that tipping more will create a sense of obligation; he’s “owed” something because he’s just dropped so much money on her. While you’re more likely to find dudes like this at strip clubs, they’re also known to frequent high-end bars and cocktail lounges.

This isn’t exclusively something women do, by the by. Male servers will also flirt for tips, especially male bartenders. In fact, there’re bars and clubs that’re notorious for hiring flirty male bartenders.

You can also find a variation on professional flirting at stores; a little light flirting keeps the customer entertained and can also encourage them to buy that item that the salesperson told them made them look so hot.

However, more often than not, what we tend to think of as flirting — especially in a professional setting — tends to just be professional niceness. Showing interest in someone is a quick and easy way to build a connection and make them feel good. Making them feel good means they’re more likely to associate that feeling with the brand, the restaurant, the store or the service. It’s one of the intangibles that can make the difference between somebody choosing to go to your practice or the doc-in-the-box down the street.

Of course, not all professional politeness and interest is strategic; some folks are just friendly like that. And of course, there are folks who will flirt because flirting is fun. They don’t mean anything by it, nor do they want anything out of it other than just enjoying flirting with someone.

It can be easy to mistake for flirting in part because, well, someone gives us attention — especially someone we find attractive — it feels great and we want it to mean more. We’re more likely to round it up to flirting because motivated reasoning is a hell of a drug and who doesn’t want to believe that Dr. McHotlips, DDS isn’t into us?

How can you tell if someone is actually interested? Well, to start with, you need a baseline to work from. Are they acting different with you than they do with other customers or other clients? If they aren’t singling you, specifically out for special and sustained attention, then probably not. The bartender who keeps coming back to talk with you, even when the bar is busy, is giving you more of an indication that they like you more than the typical customer… but that doesn’t mean that they’re necessarily interested in more than conversation.

Similarly, does their job require them to flirt? Are their wages enhanced by being perceived as being more than professionally interested? Again: the odds are better that this is professional flirting, not genuine interest.

Also: what kinds of questions are they asking? Are they asking typical getting to know you questions, or are they asking questions that might give some idea of your relationship status? Are they acting in a way that you would expect from a person who’s interested in you exclusively platonically, or are they being a little more teasing, a little more tempting? Flirting is, in a lot of ways, the dance of getting someone interested in doing something. It can help to think of flirting as trying to get somebody to jump into the pool that they’re worried may be too cold; flirting is the process of inviting them to dip their toe in and doesn’t the water look inviting? Now to be fair: asking the usual getting to know you questions can be the start of flirting. After all, much as with making small talk, you have to build up to flirting; it’s rarely a good idea to dive right in. However, someone who’s flirting will usually move past those standard questions and towards asking more personal things that might tell them if you’re single, or gauge your interest in them. Asking you your feelings about, say, Perkins, generally doesn’t rise to the level of flirting.

Asking a new client about their life, especially basic “oh, you’re new in town!” questions are all fairly standard. Hell, every dentist and hygienist I’ve ever been to has been chatty like that… made slightly more ironic by them asking those questions when wrist deep in your mouth with sharp objects. Though that is, admittedly, better than the dentist I had who thought it was the height of comedy to ask me “Is it safe? Is it safe?” during check-ups and cleanings.

But over all, the best way to determine flirting vs. professional niceness is ultimately about time. Individual signals don’t mean much on their own and they’re easy to miss. If someone is continuing to send indications of interest over a period of time — let’s say more than 10 minutes, for convenience’s sake — then that’s a better sign that they’re flirting than trying to read the tea-leaves in the questions they ask.

But, again: if flirting would get them into a metric f--k-ton of hot water, professionally and legally? Then it’s best to assume that they’re not flirting after all.

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 (m20) just made a huge mistake. I’ve been home from college for about a month now, with another two months left before in-person classes resume, and the cabin fever has set in hard. A few days ago, about half of my family started showing symptoms of COVID, leaving the rest of us to take care of them while they isolate. This has been fairly stressful, since I don’t know yet whether I might have been infected, or even if they are. On top of that, distancing myself as much as possible from other family members has exacerbated feelings of loneliness I’ve been struggling with ever since I forced myself to walk away from a frankly toxic friend group (there’s a whole lot of emotional neglect, gaslighting, and overall s--ttiness there that I’m not going to talk about here).

In what may have been the worst possible idea I’ve had in a long time, I sent a “hey, how’ve things been” text (those are the exact words) to a person I had hooked up with for a few weeks at the start of the previous semester. I wasn’t going to talk about the COVID or loneliness stuff, and I also wasn’t going to do any kind of “take me back, I miss you” routine. I had just wanted to talk to someone, maybe make a few jokes about living in a frozen hellscape to get my mind off of things, nothing serious (the idiocy at display here is only becoming more apparent as I write this). I know texting an ex is usually a bad idea, but I figured that enough time had passed and things had ended amicably enough that I thought it would be ok. Besides, I’ve been on good terms with my other exes, so I didn’t think there would be much harm in reaching out.

As it turns out, I was completely wrong. Turns out my ex had been in a new relationship ever since ours ended, and due to a previous experience with a stalker (which was bad enough that the police had to get involved and left her with some serious mental scarring), she really didn’t appreciate random texts out of the blue from exes. She told me that she wanted all communication between us to stop and for me to respect her boundaries. I of course apologized for reaching out, explained that I didn’t know about the current relationship or the stalker, and agreed to cut off communication. I also explained why I had reached out, and apologized for how my message was received, acknowledging that even though I didn’t know about the stalker or the new relationship, it was inappropriate for me to reach out. I deleted her contact information from my phone immediately after I sent the apology.

I feel terrible. I never wanted to hurt her, but I’m pretty sure that I just made her relive one of the worst experiences of her life. I’m not going to contact her ever again, obviously. I guess I’m writing you because I don’t know how much I should be beating myself up for this. On the one hand, I seriously hurt someone I cared about. On the other, I couldn’t have known this would happen and I feel like I did the best I could to repair the damage afterwards. I guess I’m kind of overwhelmed right now, and however bad I feel, I recognize that it was probably worse for her than it was for me.

Who knows, maybe this can serve as a warning for others who are about to make the same mistake.

Sincerely,

Shouldn’t’ve Texted Former hook-Up

DEAR SHOULDN’T HAVE TEXTED FORMER HOOK-UP: You didn’t f--k up, STFU. Seriously. You just had some seriously s--tty luck.

You were lonely and wanting some basic human contact, so you reached out to someone who you had reason to believe you were on fairly amicable terms with. You sent an entirely innocuous and normal text to try to get back in in touch with someone you hadn’t talked to in a while. And while it may not have exactly been the most exciting way of saying “hey, we haven’t talked in a while, so I wanted to say ‘hey'”, your text was pretty typical. 99% of the population wouldn’t blink if they got that text from someone they knew.

Everything else that happened? That’s all your ex, and was completely outside of your control. You had no way of knowing that she was in a new relationship, you had no way of knowing that she had an issue with a stalker or that getting a “hi, how are you?” text from an ex was particularly triggering for her. This was just bad luck. You stepped on a landmine that you didn’t know was there or had any reason to suspect even existed. And while it absolutely sucks that your doing this angered her  — for entirely understandable reasons —  or had echoes of her stalker, this was a pure accident. This wasn’t bad judgement, this wasn’t inappropriate, this wasn’t ignoring the warning signs, this was saying “hey” and through random chance, just happening to hit a raw wound that — again — you didn’t know was there.

And the instant she told you how much she doesn’t like hearing from exes without warning, you apologized and accepted her request that you don’t contact her again. Those were all the right things to do.

There’s nothing inappropriate with talking to an ex, especially one where the break-up was amicable. There’s nothing inappropriate about reaching out to someone you used to date in hopes of reconnecting, having a decent conversation and possibly moving towards a post-break-up friendship. This specific person has (again, completely understandable) issues surrounding random texts from exes. You didn’t know and just happened to pick the wrong person to text that day.

This was an accident, man. Would you have texted her if you’d known about any of this? Hell no you wouldn’t have, because you’re not an a--hole. It sucks that this happened and that you hurt or upset her. But this was a set of very specific circumstances that lined up in a very specific way, that aren’t likely to happen again. You’ve apologized and you’ve backed away like she asked. The only thing left to do is pick yourself up, dust yourself off and just move forward.

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 have Aspergers and never really learned any way of dealing with it. Admittedly, when I was a kid I did alright, I could get by with being the class goofball that made friends who could laugh at my weirdness.

Now that I’m a 38/M, I can’t just wear my pants on my head at recess and sing Over the Rainbow.

…right?

I’ve had a crush on this girl for a couple months now, and I have no idea what to say to keep the conversation going. We have gone to the same school since Kindergarten, though we never spoke much. She was actually my 7th grade crush.

Years passed. My mom died over 2 years ago and she contacted me about it. Everyone in the neighborhood knew my mom, she was very outgoing with everyone, kids and their parents. She and I became Facebook friends. And she’s managed to win my heart all over again and she doesn’t even know it. The problem is I don’t know how to talk to her. Our texts are very short. Sometimes she responds but then I just leave the conversation hanging. Example:

Me: What are you guys up to this weekend?

Her: Just relaxing! You?

Me: Same.

Or when she posted pictures of the light show she took the kids to…

Me: Love the pics! Worth braving the cold for?

Her: Thanks! Yes, we enjoyed it!

Me: Are you still there?

Her: No, we’re home.

Me: Okay

I have no idea what I’m doing. Am I flirting? Does she know I like her? I suck at reading people, and I don’t have any conversation skills. Oh, and she isn’t like me; She’s a normal woman without any kind of autism that I can tell. I really hope that isn’t the problem, but it could be. Being more aggressive and blunt is tough for me, too, though. I’m not one of those guys that can just walk up to a girl and be like “Hey, you and me, wanna go out?” I wish I could. Am I reaching outside of my league?

Another factor is, I don’t want to scare her off, or be too creepy.

She got out of a mentally abusive relationship with her ex husband. Similar to my own relationship with my father. I admit it still causes distress in me, dad messed me up pretty bad, But she appears to be doing better than I am. Still, I don’t want to create any red flags with her, and I want to show her I’m a good person. Maybe I’m being too cautious?

I think most of the people in my neighborhood thought I was autistic because I rarely spoke and never made eye contact. It was mostly true, I was scared to speak up for myself back then, so mom had to be my voice. I was very sheltered, even though I could take care of myself behind closed doors, mom always seemed to do everything for me in public. I worry about how that image sticks in people’s minds. But I don’t need a caretaker, I just want a partner. Someone to witness life with.

As an adult, and without mom or dad around anymore, I have changed a great deal. But I don’t feel like I erased that image everyone has of me. That “the autistic kid” is still my reputation. I worry that will be the main reason she’d reject me. I mean, that’s how I’ve been presented my whole life till now. I just wish that I had been better in the past. More outgoing. Different.

I wouldn’t want her to feel forced to talk to me, or date me. I always imagine that eventually she’ll be the one to ask me out after I’ve shown her how different I am. Yes, I’m a coward. I just don’t want to scare her away.

I have no idea what I’m doing. Any advice would be helpful!

Need My Cyrano

DEAR NEED MY CYRANO: First of all NMC, it’s good that you’ve been working on your life and making things better. That’s awesome, and you should be proud of all that you’ve accomplished. I’m just sorry that these improvements had to come around because of the loss of your mother.

So let’s talk about your situation. Like a lot of folks who write in, you have a few different things happening here, NMC. And, again, like a lot of the folks who write in, the issues you’re having aren’t the issues you THINK you’re having. However, dealing with the underlying issues will also help with the problem you’re asking about.

But let’s tease this apart a little, shall we?

On the surface, we have the issue with being unable to really get a conversation started with her. Your issue here is two-fold. The first is that, to be blunt, your conversations are boring. The first example you shared is an incredibly generic message, especially as  a way of trying to start a conversation with someone that you’re interested in. “What are you up to?” doesn’t really get the conversational ball rolling; unless she already has plans or something interesting going on, the conversation is going to grind to a halt fairly quickly because there’s nowhere to go after “just relaxing”. That’s a conversational dead-end. Plus, it tends to put the effort on getting the conversation started on her — you’re functionally asking her to choose the topic of conversation. Unless you and she already talk at length on the regular and have the sort of friendship where you shoot the s--t about nothing, it’s not going to go anywhere.

If you’re going to try to start a conversation, you do better to have a reason to either talk to her or to get her engaged with you — something that will get the conversation rolling and encourage a response.

In my book “I Got Her Number… Now What?”, one of the things I advocate is to engage someone on an emotional level — ideally something that provokes a laugh, a “wow!” or an “awww”. Something that can get the person you’re texting or messaging to laugh is a good one; laughter is one of the the things that triggers our brain to produce dopamine and oxytocin, after all. One of the ways I’ve gotten conversations started is to find a funny GIF or meme and send it with some form of commentary. An example might be a video of a snow leopard grabbing a cabbage and hauling it into a bucket with some quip — “ever loved anything as much as this cat loves cabbage?” or “getting the coleslaw ready for the BBQ like…”. It doesn’t need to be the most trenchant observation or greatest bon-mot; the laugh from the meme or video will do most of the work, and it gives you an opening to start the conversation. Hell, it can even be “I need someone else to see just how goddamn adorable this cat is.”

Other times it can be sharing a relevant (or amusing) tweet, facebook post or Reddit article. I’ve had conversations that would go on for hours that were started by sharing Am I The Asshole posts or “Look at this whacked out music video…”

Also: “same” is a lousy reply. Not only does it cut the conversation short — where do you go from there? — it’s boring. Why are you asking about her plans, when you don’t have plans either? You’re either going to come across as being bored and hoping that she’ll have plans you could latch onto, or just living a boring life. Even if you aren’t doing something, you could at least make it entertaining, something you’re looking forward to, rather than just “yeah, I got nothin’.”

If, for example, you also have no plans, it’d be better to say “I’m doing absolutely NOTHING this weekend and it is going to be GLORIOUS.” This way, it’s not “I don’t have plans”, it’s that you’re choosing to stay at home because you’d like to just relax and recharge. It’s something you’re looking forward to, rather than something you’re stuck with.

But again: it’s still better not to start the conversation with “so what are you up to?”

Just as importantly though is that in your example, you’re asking the wrong questions. The questions you’re asking can all be answered in three words or less — and most often in one. The worst questions to ask are binary questions, where they can be answered with a “yes” or “no”. Those are conversational dead-ends because there’s nowhere to go from there. “How was it?” “Fine” “Was it cold?” “Yeah”. None of that facilitates conversation. You want to ask open-ended questions, ones that invite more participation and conversation. Instead of saying “how was it” with the lights, you’d be better asking about which were her favorites, or did she ever used to go to these as a kid? You could even prompt things with sending a video of one of those super-elaborate Christmas light setups that people coordinate to music with a comment like “one of these days I want to do this to my house”.

By focusing on engaging with her emotionally and asking more interesting open-ended questions, you’re in a better position to get the conversation going and find opportunities to connect, flirt and possibly even ask her out on a date.

But those are surface issues. The bigger issues here are a) whether there’s a connection or interest there at all and b) your own self-perception.

The former is the tough part. If I’m being honest, it sounds like this is a fairly shallow connection. I’m not saying that she doesn’t think you’re a great guy, but the conversations you’ve been showing have been the polite small-talk variety, not the “I want to hear more” or “Let’s keep the conversation going, maybe over coffee?” kind.

Which… well, that’s going to be life. Sometimes you’ll have folks who you crush on, who like you as a person but who just aren’t into you that way. And that’s fine. It sucks… but it’s normal and it happens to everyone. Part of life, dating and finding a partner is learning to navigate those particular waters and not let it wreck your s--t.

The tricky part is not getting hung up on one person, especially one person who’s been a long-term crush.

I suspect part of why you’re hung up on her is as much about what she represents as it is about her as a person. I mean, don’t get me wrong: I’m sure she’s a lovely and wonderful person. But it sounds like it’s as much a case of “the one that got away” and her having reached out first (even under tragic circumstances) as it is about the things that make her special. A lot of times when folks have the “I have a crush on her and she doesn’t know”, it tends to be a case of her representing something specific to them — an aspirational goal, a way of fulfilling thwarted dreams, even just “the first one to be nice to me”. That makes people less likely to act on those crushes because a relationship in potentia can’t be ruined. It can be as perfect as you want it to be because it ultimately is all in your head. Trying to act on it — asking her out on a date, making a move, even just indicating that you’re attracted to them — makes it real. And if it’s real, then it can fail. It can fall apart. Or, worse, you can get rejected. When you’re always on the edge of “But how should I tell her” and the answer isn’t just saying “hey, I’m doing $COOL_THING on Friday and I’d love to take you,” then it’s a pretty good sign that the thing holding you back tends to be a fear of losing the fantasy.

In fact, that’s often a big part of why folks hold back and wish that their crush would notice and then do the work for them; that’s part of the fantasy. They don’t have to do anything, just demonstrate how awesome they are and their crush would swoon and take the responsibility for everything.

Unfortunately… that doesn’t happen, and it can’t happen unless you are an active participant in your own life. And that means not waiting or relying on them to notice you or hoping that if you think at them hard enough, your mutant powers will suddenly kick in and they’ll be able to hear your thoughts and realize you’re just too shy or whatever.

And honestly, that’s where your third issue comes in. You worry that your reputation or label as a child, accurate or not, is holding you back and you want to know how to erase that image. Now, first and foremost: you really don’t know or even have any reason to believe that this is the case. Hell, it doesn’t sound like it was an issue then or is one now, and it certainly isn’t something you need to “live down” or try to prove you’ve grown past.

But on a more general level, people often wonder how to move past other folks’ perceptions of who they were back in the day. Sometimes it’s trying to overcome having been a s--tty person back in high-school. Other times it’s trying to tell people that you’re cool now, not the dork you were way back when. The answer there is, ultimately, very simple: you show people who you actually are. But, as with connecting with people, with flirting or just asking someone out on a date… you have to make an active choice to do this. If you’re more outgoing now or more adventurous or self-sufficient, more self-aware, more socially adept or what-have-you, then demonstrate it. Not in the show-off sense, but simply having an active life. Going out, hanging out with friends (when it’s safe to go out and hang out with friends again, granted), inviting folks to do things or hosting events yourself… these are all ways of showing that you aren’t the person people thought you were back in the day.

But here’s the thing: all this? It ties nicely into things like, say, being more effective at texting and communicating with folks you’re interested in. Starting the conversation with “Wow, you are not going to believe the crazy thing that happened to me this weekend” and being able to relay this whacky, fun or cool story to your crush tags the bases we were just talking about. It provokes a response by creating an open loop (well, what crazy thing happened?). It invites participation and questions from her, and opens up the chance to ask her open-ended questions. Texts like this give you a chance to demonstrate what your life is like now (hey, look at the stuff you’re doing!) in a way that doesn’t come off as fake, forced or braggy. And, as a bonus, it gives you an opening to invite her to do something down the line — “Yeah, I’m going back next weekend. You know, I think you’d really dig it; would you like to come along?”

But again: all of that is going to rely on your taking an active role and directing your life yourself, not just hoping that your crush is going to notice you and spare you the effort of having to take any risks. There is no reward without risk, no success without the chance of failure. If you want to make things happen with your crush — or anyone else, for that matter — you have to be willing to stop defining yourself as “the guy who couldn’t make the move” or hoping they’ll notice. You have to put yourself out there, own your interest and take your shot. If you want things to happen, you have to roll the dice and move your mice. Otherwise… you’re just not even in the game.

Good luck.

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