DEAR DR. NERDLOVE: I’m a young woman and I recently began working at a new job. Right from my first day working there, the confident popular co-worker, who is kind of a “bad boy”, (I’m going to call him C to make this quicker) showed interest in me. C was kind to me, flirted with me, always tried to touch me, and just did all the types of things you’d associate with attraction. I didn’t like him back though, if anything I kind of resented him for giving me all this extra attention when all I wanted to do was to be left alone. I can be quite shy and socially-awkward when I’m first meeting new people and am adjusting to a new environment.

However, as I continually showed zero interest in C, he persisted;  although his efforts became less and less, it never went away. Later on, C was going through some personal issues, and he became very withdrawn and quiet. Eventually, he snapped out of it, but when he did his feelings for me seem to have disappeared. Also, during this period I had become much more confident and comfortable with my surroundings.

Although he pays some special attention to me now (not much), it is nothing compared to how much he used to. Lately, I’ve been thinking I might have some feelings for C, I miss the way he used to treat me. Does C still like me and is just giving me a taste of my own medicine by playing hard to get? Or has he really just lost interest? Does he not like me anymore because I’ve become less shy?

What should I do?

Thanks,

Hunted Becomes The Hunter

DEAR HUNTED BECOMES THE HUNTER: So before I get to your letter HTH, I’m going to go on a bit of a rant here. Because frankly there’re few dating strategies that make me twitch uncontrollably more than “playing hard to get”.

Now there’s some legitimate science behind the strategy; obstacles in the path to fulfillment tend to make us crave it more. And, in fairness, using a little “want this? Can’t have it…” is a useful tool when it comes to flirting. Building rapport then breaking it is a way of building sexual tension and increasing excitement until you’ve both reached the bursting point. However, there quickly comes a point where it goes from a flirty tease to a pointless exercise in trying to maintain an air of artificial scarcity for ultimately bulls

t reasons. The infamous “Rules” for example, insisted that being too available — which is to say, wanting to see someone as much as they wanted to see you — would inevitably diminish men’s interest in women. Similarly, men get taught that showing interest in women they want to date or sleep with gives up some vital advantage, because “who cares less, has the power”.

Honestly, the older I get, the less time and patience I have with these sorts of games. While playful teasing and utilizing a push-pull dynamic during flirting can be a powerful and useful technique for building attraction, throwing up artificial barriers only serves to hinder communication and makes people miserable in the process. Folks who play hard to get tend to get very surprised when the people take “not interested” for an answer and move on.

Which brings us back around to your friend C. I don’t think he’s playing hard to get or giving you a taste of your own medicine; I think he — finally — took your lack of interest for an answer and decided to quit hitting on you.

I mean, for weeks you were giving him him negative feedback. You made it clear that you weren’t interested and likely were giving off some serious “knock it the f

k off/touch me again and you pull back a bloody stump” vibes. Even for someone who’s only flirting for fun, there’s inevitably going to come a point where they hear “p*ss off” and decide to take it seriously.

(There’s a discussion to be had about just how long C was hanging in there and the appropriateness of his behavior in a professional setting, but that’s another column entirely).

And just between you, me and everyone reading this: it’s a little unfair to turn around and say “wait, I don’t want the flirting to stop” after you spent all that time telling him you weren’t interested. I get that you take time to warm up to folks and needed to adjust to a new environment… but he doesn’t know that. He just knows that you haven’t appreciated his flirty behavior and he’s decided to dial it back. Maybe his personal crisis had something to do with it, maybe someone in HR had a very pointed conversation with him, who knows. The point is: if you want him to know that you kinda like the flirting now and want it to start up again… well, you’re gonna have to let him know. Think of it like a stand-offish cat letting its human that maybe it’s ready for some light head scratches; you want him to know that hey, you’re cool with a little flirting now.

How do you do that? Well, while you could signal that you’re cool with it by responding more positively to what flirting he does now… the better option is to simply use your words. You can let him know that you needed to acclimate to your new job and you’re the sort of person who needs to get comfortable before you’re able to handle a lot of attention. You can also let him know that hey, you’re actually ok with a little more flirting now and that you even miss it a little. Then you take a step back and let him decide what his next step is going to be. If it’s a case that he’s lost interest… well this is something that can be chalked up to unfortunate timing. But if he is still interested, then now he knows he has a green light for continuing and he can begin giving you attention in the ways you’re ready to receive.

But none of that can happen unless the two of you actually clear the air. Someone’s gonna have to make the first move here. Might as well be you.

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 tried to break up with my girlfriend of one year last night, and after telling her I loved her, but I wasn’t in love with her, I started to cry and feel pain from it. She asked me why I was hurting so badly if this is something I wanted.

Some history on her side… she’s had more negative experiences than I’ve ever heard happen to someone. Bounced across the nation as a child because her broken family didn’t want her, had a series of really bad relationships as a young adult, got married, decided she was polyamorous for a while, then got into a series of really abusive relationships.

When her and I got together, she was raped by one of her exes, and I know that it caused a massive amount of trauma. I’ve been trying to be supportive of her. She’s not been able to hold a job for longer than a few months, has a lot of enmity towards people as a whole, and I feel like she’s needed something truly stable and solid in her life to act as a support.

We have been together a year now, and I feel like things have deteriorated. I have borne witness to emotional outburst with her while in public, been called names, and was told (in anger during our latest fight) that her dog comes before everyone else, that she’s been the only constant in her life, that her dog is the only one who’s never left her… that she could kick her dog, and the dog would still never leave (she doesn’t, mind you). When I tried to leave her last night, we both cried and hugged and said we were sorry for all the things said, and that I changed my mind and I love her, but we need to work on communicating, me being myself, and her being the best her she can be… but now, after the exhaustion has worn off, and I’ve woken up from a night’s sleep, I feel like I did right before I told her I wanted to end it… she’s staying with a friend for a day or two, and I’m here at home alone.

What do I do? Am I being manipulated? Am I not giving her the chance to heal and prove herself to me? Am I being a coward? Do I tell her “it’s not you it’s me”? I am so lost right now, I feel like I’m in an emotional storm with just a dingy, no oars, no sail, no life preserver… she’s had a VERY troubled past, much of which wasn’t her fault. Am I being unfair to her? I need help…

Sincerely,

Without a Compass

DEAR WITHOUT A COMPASS: Let’s be honest here, WAC: your relationship’s already over. You’ve got a foot out the door already. The only question remaining is how long it’s going to take before this relationship actually ends.

And that’s why you wrote to me. You want permission to pull the trigger on this.

I get that you feel bad about wanting to end things. Breaking up with someone can be incredibly difficult, even when you know it’s something that you need to do. You don’t want to be the bad guy. You start to second-guess your reasons for breaking up with them and wondering if they’re legitimate or not. You start coming up with reasons why you shouldn’t leave and why the things that make you want to leave aren’t bad enough for you to go.

Here’s what you need to legitimately break up with someone: you want it to be over. You can break up with someone for any reason. The reasons may not be “good” in the sense that you can point to them and have strangers say “yes, you should definitely leave”, but that’s ok. Break-ups aren’t like passing legislature; people don’t get to vote on your motion to leave or veto your break-up. If you want out, then you want out. Staying in to make a point or until you have a “legitimate” reason just makes it worse. Hell, imagine how it feels for your partner when you do finally leave and they realize that for the last however-long it was, you’ve been dying inside.

Now, if it helps: you sound like you’re being treated pretty badly. Blowing up at you, weaponizing your guilt at how you feel… that’s all damn s

tty. I empathize with your girlfriend for the s

t she’s gone through. She’s had it rough, and that’s a tragedy. But at the same time, having had a troubled past doesn’t give someone license to be an asshole to people who care about them.

What you need to do now is to end things, quickly and cleanly. It’s the kindest option. It’s going to hurt – it’s pretty much impossible to break up with someone and not have it hurt – but it’s better to make it fast than to drag it out. While in general I’m a proponent of giving your about-to-be ex an explanation, sometimes the only reason is “I’m done”.  And you, WAC? You’re done.

Do her the dignity of making it fast and direct. If you’re really worried about her, then give her friends or her parents a heads up that she’ll need them in the coming weeks. But stop waiting around and do what you know needs to happen.

Good luck.

DEAR DR. NERDLOVE: My question is short but it’s been really bugging me.

I’m a 24 year old (mostly) straight male, social enough with a good group of friends and a reasonable past with women. I’ve had ups and downs but I’ve always said what I meant and tried to be sincere as possible. It’s been a little more difficult lately though.

Over the past year, I’ve come to realize I have some pretty strong feelings for one of the women in my group. She’s great and a good friend, we click really well though I’m savvy enough to see that she hasn’t displayed the slightest interest in me like that. She’s ace, too, though not aromantic, far as I know.

So my question is this- do I tell her about these feelings?

There’s a little bit of hope in my heart she might give it a chance but not much. If she doesn’t, I won’t be too devastated or anything. We’re both so far back on the scale of chill that I’m sure it won’t be awkward or anything. That’s just not me and not her either. We let things go easy. So that’s not a problem.

It’s more that I don’t want to put the pressure on her. I KNOW she’s going to feel bad saying no. But I really want her to know that she’s amazing and every bit of deserving of that kind of affection. It’ll be tough but the communication of those feelings is important. I want to learn about myself through that communication and hopefully she’ll learn something about herself. To be clear, that does NOT mean “she’ll learn she liked me all along!” Just maybe something, anything about life, ideas, feelings, romance. Is it worth saying something or should I just say nothing?

Thanks.

Hoping For The Best

DEAR HOPING FOR THE BEST: You know, if it was “Should I ask her out on a date”, I’d tell you to go for it. That’s fairly simple; either she says “yes” or “no” and the two of you go on about your lives with minimal awkwardness afterwards. But confessing your feelings for someone? That’s a different story altogether.

Let’s game this out for a second HFTB. Let’s set aside the fact that she’s asexual, if not aromantic. What, exactly is your goal in telling her how you feel?

You’ve already said that she’s given you absolutely no indications that she’s into you romantically. So… what do you think you’ll gain here? Are you hoping that your confession is going to make her want to give it a shot, despite not being romantically interested in you? If it’s just about your journey – learning about yourself through telling her – then you’re using her as a prop in your own adventure of self-discovery and that’s kind of a s

tty thing to do to a friend. What is it she’s going to learn about herself by having a platonic friend tell her he’s interested in her? Because, your protests to the contrary, it sounds like you’re hoping she’s going to change her mind about how she feels about you.

Let’s zoom in on this bit here: “I KNOW she’s going to feel bad saying no. But I really want her to know that she’s amazing and every bit of deserving of that kind of affection.” So… you feel like she doesn’t know this already? Like she needs your validation to feel that way, despite no indication in your letter that she doesn’t believe that she deserves love and affection? Because that sounds like you’re hoping that that this confession is going to trigger some grand revelation in her that will… what, exactly? Change her sexuality? Confessions of love aren’t magic. Unless they’re already interested in you, it isn’t going to change how they feel. Hell, most of the time, they already know; lots of people have the experience of trying to ignore someone’s crush and hope they don’t have to actually do anything about it. And to be perfectly honest, that’s 99% of what your friend’s going to learn about herself: what it’s like being stuck in an awkward position like this.

This isn’t something that needs to happen, HTFB. You’re not going to die if she doesn’t know how you feel. You don’t have a long-simmering relationship punctuated by moments of “Can’t Spit It Out”. If you just let things continue as they are… well, things will continue as they are and you’ll still be friends. You’re letting your hope that your love is so magical that it’ll overcome what you already know to be true: she just isn’t into you that way. So put “we’ll learn something about ourselves” rationalizing away. If you like her and don’t want to make her feel bad or put pressure on her, then just enjoy the friendship you already have.

A crush isn’t a mandate to act, and friends are pretty damn awesome. Don’t mess that up.

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 wanted to reach out to you because I’m seeking guidance on a potential relationship, but am uncertain of how to proceed.

About 2-3 years ago, I went with a friend to a nearby bar, which featured a “Taco Tuesday” special after we had both seen “Sorry to Bother You,” and wanted to discuss it further. Needless to say, the bartender working that night was sociable (especially once I showed an interest in her work and craft) and overall it was a good time.

A year or so later, I came back to the bar one night to meet some other friends. Once again, she was working there and seemed happy to see me. We caught up a bit, and much to my surprise, comped me for one of my drinks, which was sweet and generous of her. This back-and-forth carried on throughout the rest of last year. I’d show up, eat, drink, tip generously, and talk. It turned out we had a good amount in common: she’s a photographer, I crew on film/video jobs. We both love talking mixology and different liquors and liqueurs.

In short, I developed a bit of a crush on this bartender. And after introducing her to some of my friends, they also picked up on a potential mutual interest vibe. So near the end of last year, I expressed an interest in hanging out with her outside of her workplace. She, much to my surprise, gave me her cell phone number and seemed willing to meet. She did express a desire to keep it casual, however, although that was not a deal-breaker for me. As someone who has to be friendly and sociable to keep working, making friends is always easier and slightly more comfortable to me.

So I reached out to her at the beginning of this year to see if she wanted to get coffee. She did text back that she was in favor of it, but we never got a date or time pinned down, so I let it go, not wanting to pressure her. Fast-forward to now, where I stopped into her bar for a meal and some drinks. She was working there and seemed very happy to see me, so much so that she came around the bar to sit next to me as we both talked about our lives. At this point, even I felt like there was some kind of chemistry between us, and this was before the liquor started flowing.

Later on, I sent her an invite by way of a text message to a casual event among friends, but she didn’t respond, though I didn’t take it personally. Given her desire to keep things simple, I figured pushing her for an answer wouldn’t be helpful.

So in summary, I’ve been interested in getting to know this bartender a bit more outside of the place she works. We have common interests and goals, and seem to get along well enough when at her workplace. The question is where the boundaries for this relationship are.

If it can be romantic, that would be fantastic. If it’s more of a friendship, I would also enjoy it greatly, since I find myself cherishing those the most. If it’s more of a casual acquaintance-type of deal, I also would be willing to accept it, since the matter would be settled. The issue comes down to asking whether there’s room for this relationship to grow at all outside of the bar.

I’ve read enough articles and essays to know how often women have to be diplomatic when refusing the advances of men, and the difficulties of navigating that space safely. Therefore, I’ve tried to avoid overstepping my bounds with her or violating what trust I’ve earned.

Any advice or help you could provide here would be greatly appreciated.

Thank you,

-Searching for Boundaries

DEAR SEARCHING FOR BOUNDARIES: So, there’s a couple things going on here, SfB.  But before I get to your question in specifically, I want to talk a little about flirting with folks in the service industry, especially bartenders, waitstaff and the like.

While a lot of folks have issues with “is she flirting or just being friendly”, this can be particularly fraught when it comes to flirting with your bartender, your waitress or other people in service jobs. There’re a lot of things that will be working against you — both in terms of gauging her interest but also the likelihood of her being interested in you at all.

The first is that you’ve been flirting with someone in the service industry and, in particular, someone who makes a living off customers’ tips. This is something that guys in general need to keep in mind when they’re flirting with waitstaff, bartenders, shot girls, strippers and other folks who make money from tips and commissions; they have a vested interest in appearing available and interested. That means that she has a vested interest in being “professionally” flirty. By being a little friendlier and flirtier, especially with male customers, she increases the likelihood of getting more and larger tips from folks. Some will be from people who think that that they can essentially “buy” her affections, others from folks who’re likely to give more money because they’re turned on. It may feel like they’re into you… but a lot of times that’s a case of wishful thinking and letting your dick do the thinking for you. It’s important to keep a relatively level and skeptical head in these situations.

There’s also the fact that she’s at work, and in a position where she can’t be as straight-forward with turning somebody down. While there is a movement for more venues to implement “have your staff’s back at all times” policies, there’re still plenty of managers and bosses who’ll fire an employee who’s “causing trouble”, even if the trouble in this case is a customer who’s acting like a double-stuffed dickbag. So the odds are high that you’re going to get a very soft “no” – being turned down in an indirect manner. This may be a “I can’t this week”, “I’m too busy” or even a “we have a no dating customers rule”. This sort of refusal helps ease the sting of the rejection and soothes the potentially ruffled feathers of a customer who might have a profoundly negative reaction to being turned down.

The next thing to keep in mind is that as an attractive woman in a front-of-house job like bartending, she’s getting hit on a lot. There are a lot of men who are going to be throwing attention her way, and that can end up being both exhausting and tedious; doubly so because frankly, a lot of the folks hitting on her are douchebags who don’t give a six-legged rat’s ass that she’s, y’know. At work. So while she may be the most attractive woman you’ve ever met and you’ve never done anything like this before… you’re likely not even the fourth or fifth person to hit on her that day. Being yet another dude throwing dick her way makes you blend into the crowd of all the other folks who’ve made the same offer.

Now this doesn’t mean that approaching or flirting with with the waitstaff or the bartender (or whomever) is impossible; it just means that you shouldn’t, as a general rule, expect more than just some enjoyable flirting.

(And also, tip them well; they’re working hard for their money and service industry wages are a goddamn crime.)

It is possible that you and someone in the service industry might make a solid connection that could lead somewhere… but it’s going to take time and a lot of careful behavior.

Much like in your case SfB: you basically did everything right if you want to build a connection with a bartender. You became a regular, which mean that she got to know you over time. As many an advertising executive can tell you: repeated exposure breeds familiarity and familiarity breeds interest. You also made a point of being the sort of customer that waitstaff and bartenders like: you’re polite, you’re friendly, you show interest in them as a person and — importantly — you respect their time. You tip well, you’re well mannered… these are these are the sorts of things that makes somebody a favorite regular.

Once you’ve built up that respect, affection and — importantly — trust over time, then and only then did you make an offer to get together outside of work. And even then… you did it all correctly. You didn’t treat not being able to make a date work as anything other than an unfortunate case of bad timing and incompatible schedules. You didn’t push her, get angry or otherwise act like an asshat. All to the good. This is a big part of why she’s still happy to see you when you come in.

The only mistake that you made — as far as such things go — is that you invited her to a group event. While that’s not necessarily a bad thing — in fact, it can work out rather well — it can also be more than a little intimidating for some folks. Going to an event where you only know one person can be a little much, especially when you don’t necessarily know that person well. It can be intimidating if they’re a little on the shy side (which yes, even folks with social jobs like bartending can be, especially when they’re not in work mode) or exhausting if they’re an introvert. And some of it might have been an issue of “private event” vs “public event”. If it were you and some friends going to something that was open to the general public, that might be more acceptable than if it were a casual get together at somebody’s house; it’s entirely possible she might have felt like an outsider or intruder.

Or it just may not be to her taste. Or… well, she just might not have been interested.

But again: you’ve handled this well, and that says a lot of good things about you.

Here’s what I’d suggest: give it one more shot with your bartender friend. This time, the next time you hang out that the bar, bring up something that you’re planning to do anyway: a concert, an art show, a street-faire… something that you enjoy and would go to regardless of whether you have a date or not. Then, towards the end of the evening when you’re planning on heading out… tell her that you think she’d probably really enjoy $COOL_THING and if she’s interested, you’d love to take her. This has a number of advantages over inviting someone to a casual get-together with strangers: there’s a specific time and place, it’s lower emotional stakes and it feels less serious. It’s a public event, which can feel both safer and less intense, and it doesn’t feel like as much of an investment.

If she’s down… well, Yahtzee; you both win. If not? Then assume that this was a soft “no” and that while she likes you as a person and a regular at her bar, she’s not interested in taking things outside of work. You can take satisfaction with having not thrown away your shot and in having gotten an answer. By respecting the soft no, you’re respecting her and not making things awkward and having to find a new bar.

And if it is a case of her being interested, but circumstances have worked against you? Well, she knows you’re into her and that you’re a cool and respectful dude. She’ll let you know if she’s down for this being more than just a bartender/favorite customer relationship.’

Good luck.

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