DEAR DR. NERDLOVE: I’ve been an avid reader for a while and your advice has helped me understand some things about relationships. My current issue basically boils down to some miscommunication that ultimately led to 1.5 years of going after a girl (yeah, I know) ending quite abruptly.

So I met this girl (who happens to be Indian and I’m white) when she joined my workplace which is already a dicey situation for romance. I quickly developed an interest in her and it seemed like we hit it off pretty well. Normally, I would just ask her out on a date but with the workplace situation I was concerned with the possible career ramifications if things go awry or she bristled at the notion of me asking her out. So I foolishly decided that it would be an okay idea to play the long game.

We hung out with others more in the beginning but she then asked me if I wanted to go on a day trip hiking with her. Of course I’m thinking, “Hmm, does she just want to go with someone on the hike or was she asking me specifically?” Things went well but never really took off from there (which is difficult what with me making very oblique references to my interest in her).

After some time she stopped asking me out and it was just me trying to keep things alive. Furthermore, while should used to respond quickly to my texts to hang out with a resounding yes (I’m always looking for that “soft no” but didn’t believe I could find it), hours would now pass before a response. This then got to a weird situation where I would ask her to hang out, she would say yes, and then repeatedly flake on me the day of with some excuse which didn’t seem probable given how many times it happened (why does she do this? Couldn’t she give me a soft no instead of blowing my plans on the weekend? Or did she change her mind after the fact?).

Fast forward to last week where we had made plans again (which I had finally decided to ask her out after moving to separate teams) only to have her say that, in fact, she was moving out of her apartment that day and couldn’t go. She’s says, “Let’s try next weekend!”. The next weekend (yeah, I can’t help myself) I take her up on that offer and she says she can’t because her relatives are in town to help her with wedding shopping because she is getting married! Well, that felt like the most powerful sucker punch I’d ever taken. The wedding planning had apparently been going on for several months and I was just informed via canceling our plans.

Now, I don’t know if there were cultural aspects at play that really tripped me up in concert with the fact that I’m not experienced in the dating game myself. Can you help me put this whole thing in perspective? Did it ever seem like there was a chance with us or did she always see me as a friend at best? How did the whole work situation influence things? What was the deal with the flaking; that’s not okay, right? Why did she wait so long to tell me she was getting married? Did I blow this whole thing up in my head much bigger than it was?

Thanks,

– Mystifyingly Mixed Messages

DEAR MYSTIFYINGLY MIXED MESSAGES: You made this into a bigger deal than it was, M3.

Here’s what happened in a nutshell: she most likely saw you as a friend at first. She asked you out on an outing – whether it was a date or not (hey, hiking can make an excellent first date!) is up in the air, since likely neither of you really attempted to clarify the situation – but it’s pretty clear you saw this as more than she did. After the hike, she apparently decided that she wasn’t into you for some reason. She just may have decided she wasn’t attracted to you. She may have gotten the hint that you were more into her than she was. Or who knows, maybe she got into a relationship with someone else around the same time.

Regardless, she was trying to give you the wave-off without being direct about it. Hence the delays in responses to your texts, the last-minute flakes, etc. She was trying to do a version of The Fade-Out and hoping that you were going to get the hint. Whether she was doing it well is another question entirely, but the fact remains that she was telling you she wasn’t interested without actually coming out and saying it.

Making plans you have no intention of following up on and flaking at the last minute is almost cartoonishly rude. Like, to the point of bad sitcom character levels of antisocial behavior. Better to just say “no, thanks,” or “Hey, I’m seeing someone” or “I’m clinically dead and infested by lizards” than to constantly say “ok, sure” and then pull a no-show on the day of.

Why was she doing this? She could be just that inconsiderate. I doubt it, but it’s a possibility. My rule of thumb, however, is to not attribute to malice that which could equally be attributed to social awkwardness. And believe me, women can be just as socially awkward as men can.

What I suspect is that she’s severely conflict averse under the best of circumstances. It’s entirely possible – likely even – that when you’d ask her out in person, she felt like she couldn’t refuse gracefully or didn’t know how to. When in a situation where you’re constantly up in each other’s business, such as when you work closely together, it’s a little harder to do the “I’m too busy” line when it’s entirely possible that you’ll hear about her real plans through the company grapevine. It can also feel more difficult to take a hard-line refusal with someone you have to see every day; you may worry that it’d directly impact your work life.

So: seriously rude behavior… but I doubt there was any ill-intent behind it, just someone being bad at handling conflict and confrontation no matter how mild.

TL;DR: she wasn’t interested and you weren’t getting the hint. It would’ve been much better all around for her to be direct (or at least more overt) and not constantly blowing you off. But what’s done is done. There wasn’t much you could do to prevent her flaking on you. The best thing you could’ve done is to simply move on.

Just remember: flaking is like unreturned messages. Once is happenstance. Twice is coincidence. Three times is enemy action her sending you a message.

Better luck next time, M3.

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 a geeky girl in college, a gamer, very socially active, and generally a direct person.  I’ve been asked out a few times at parties and I’d like to switch things up by asking (other geeky) guys out myself, but… there’s always a but.

What’s holding me back is, well, sex.  Or more like expectations about sex.  The impression I’ve generally gotten is that the older my peers are, the less time they wait before having sex.  I’d like to date and get to know some guys, but I’m not interested in hooking up or doing anything sexual with a relative acquaintance or someone I’m not in at least a semi-serious relationship with.  The other thing is that if a woman is forward and initiates contact, the expectation seems to be that she’s experienced and well aware of how to flirt, and I don’t really have any experience with guys romantically or sexually.  

So basically, how do I flirt with guys and ask them out while making it clear we’re not about to tumble into bed at the end of the first date… or the second… and so on without scaring them off?  And while minimizing potential awkward and misunderstandings.  I’m not looking to ~wait til marriage~ or set a strict time for when I’m down to do what, but I know I wouldn’t feel comfortable being intimate with someone I’m not already close to.

Takes Her Time

DEAR TAKES HER TIME: It’s pretty simple, THT; you just tell ’em.

Now, it’s true that there are a lot of guys who expect some sort of accelerated time-table when it comes to sex; some will expect it as soon as humanly possible, others have their own version of the three date rule, where if the girl doesn’t put out within three dates, he moves on to the next one in line.

Thing is: this isn’t all men by any stretch of the imagination. I mean, yeah, just about every guy out there will want sex as quickly as he can get it… after all, sex is pretty damn awesome when you do it right. But just because we’re willing to bang out as soon as it’s offered doesn’t mean that there aren’t plenty of guys who will quite happily take the time that is required for the two of you to reach the level comfort and intimacy you feel you need before you’re ready to sleep with him.

Don’t let random bullshit ideas about gender roles hold you back from being willing to make the first move. Just because you were willing to approach a guy doesn’t automatically mean that you’re obligated to move faster than you feel comfortable with.

Now, as for how you tell them? Well, you said it pretty well in your letter. “I’m not looking to ~wait til marriage~ or set a strict time for when I’m down to do what, but I know I wouldn’t feel comfortable being intimate with someone I’m not already close to,” is concise, to the point and sets up exactly what to expect.

When you tell them can be tricky; you don’t really want to blurt it out between the endive salad and the coq au vin, when it would be a bit of a non-sequitur but you also don’t want to wait until his pants are around his ankles and he’s giving you then “Eh? Eh?” head-gestures.  I would recommend relatively soon into the first significant make-out session; some time after the first good-night kiss and before he’s going for some under-the-shirt action. Pull back a second and let him know where you stand.

And don’t stress out about chasing guys off or standing firm. A guy who isn’t willing to accept your limits is not a guy you want to date. If knowing he’s not getting a beej by the second date is going to make him look for other pastures, you really aren’t suffering any great loss. He’s just putting you one more step closer to finding a guy who is right for you.

Good luck.

DEAR DR. NERDLOVE: I have a question about “Friends with Benefits” relationships. An old friend and I have slipped into one of these after drunkenly hooking up one night. I have no interest in dating her at all and she says that she is ok with that, and she just wants to hook up.

However I’m really nervous now because this relationship is secret and we basically have the same circle of friends. And I’ve heard from people that these types of relationships always end in disaster. While I’m enjoying the “benefits” of this relationship, is it really destined to end terribly? And when I meet a girl that i want to start a real relationship with, do you think we will be able to end it with her without hurt feelings?

Threading The Needle

DEAR THREADING THE NEEDLE: Here’s the secret to making a casual or FWB relationship work: put less emphasis on the “casual” or “with benefits” part and more on the “friend” and “relationship” parts.

The single biggest reason why casual relationships end with people being hurt is because people treat the “casual” label as an excuse to treat the person they’re in the relationship casually. There’s a tendency to see casual relationships or FWBs as less “real” or “meaningful” than more traditional, committed relationships and, as a result, we get careless with other people’s feelings in ways we wouldn’t if we slapped the “boyfriend/girlfriend” label on it.

Even if the relationship is purely sexual and you are both aware that nothing else will ever come of it, that doesn’t mean that the only thing to do is show up, have sex, wipe yourself off on the curtains and take off. You may not want to go on romantic, candle-lit dinners or trips to gorgeous, secluded B&Bs, but that doesn’t mean you shouldn’t be treating the person you’re banging with respect and friendship.

Hell, even if you both agree that you’re doing this to scratch an itch, nobody likes being treated like a human-shaped sex-toy (with the exception of having actually agreed to that up front, anyway). That’s a great way to turn an enjoyable and fulfilling relationship into something filled with regret and remorse.

The way you keep a FWB relationship from ending badly is the same way you keep any other relationship from ending badly: open communication and honesty. Be straight forward with how you feel, be open and receptive to how she feels. Keep those lines of communication open and make sure that she knows that she can talk to you about the relationship. Hell, it may not be a bad idea to have occasional check-ins to make sure you’re both getting your needs met and you’re on the same page.

Want to know how to poison a FWB relationship from the get-go? Treat it as something shameful or something that’s doomed. I can appreciate wanting to be discrete, but you need to keep in mind: this isn’t about how your friends may feel, this is about the two of you. It’s up to you two to decide what the rules are for your relationship; nobody else gets a say.

And while I totally can understand the fun of having a dirty little secret, sometimes the stress of keeping things on the down-low can overtake the thrill of sneaking around.

Part of the way you can negate any potential drama from people finding out is by not treating it like a shameful secret you two have to take to the grave. You may not want to make out in front of your friends, but you don’t have to pretend like you aren’t banging, especially if folks ask. A good rule of thumb when it comes to avoiding drama is to not treat this like a big deal. You’re friends, occasionally you hook up, it’s all good. If your friends aren’t the type of people who can understand that not every relationship has to be moving towards the white-picket-fence/two-cars/two-point-five-kids goal and are going to give you s

t for that… well, it may be time to consider whether these are friends you want in your life.

But here’s the thing: every relationship ends until one doesn’t. Friends with benefits relationships always end one of two ways: either you quit having sex, or you quit being friends. This doesn’t mean you’re doomed either way. You may decide to stop having sex because one of you has fallen for someone else, or because you decide the sexual side of your friendship has come to it’s natural and mutual conclusion. You may stop being friends because you fell in love and now you’re “officially” dating… hell, you may drift apart naturally, for reasons that have nothing to do with the fact that you were sleeping together.

It’s impossible to say whether you would be able to end the sexual aspect of your relationship without pain or tears – there’re so many variables that you’d get better results rolling a d20 and hoping to make your Save Vs. Drama (with advantage). But then again: there are no guarantees that you can end ANY type of relationship, sexual or platonic, without hurt feelings. All I can say is that being a stand-up, honest and compassionate guy will make things easier regardless of how it ends.

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 a geek girl with a problem. I’m super attracted to geeks, mostly because of the whole similar interests thing. As you have said sometimes geeks are shy, I’m pretty shy too, but I’ve finally gotten to the point where I am more comfortable asking people out. I was told (by an ex) that relationships never work out when a girl makes the first move, it sounds ridiculous in my head, but could he be right? Obviously I haven’t had a relationship work out (or I likely wouldn’t be looking for a new one) but I haven’t had someone I’ve asked out work out at all. Am I doing something wrong? Should I still stay shy?

Shrinking Violet

DEAR SHRINKING VIOLET: To put it mildly, your ex is an idiot.

There are any number of reasons why a relationship might not work out whether it’s because of sexual incompatibility, emotional disconnects or even just your lives going in different directions. The idea that a relationship won’t work based on who asked whom out first? You might as well insist that you can’t ask someone out on days where you see a pigeon take a s

t while flying east-northeast because the relationship will never work; you’ll have about the same level of accuracy.

To steal a line from my celebrity Patronus, every relationship fails until one doesn’t. The idea that a woman asking a man out automatically dooms a relationship is a) bulls

t and b) really amusing when you get all of the dudes complaining about why women “don’t approach more“.

I know people who come up with all sorts of contrived “rules” about when you can ask people out and when you can’t, whether it’s within a three month span between Christmas and Valentine’s Day or within X days/weeks/months of someone else asking them out because of some bulls

t reason and it all comes down to magical thinking and confirmation bias.

If you like a dude and you’re moved to ask him out, then by all means, do so! The only thing I would caution you about is that some guys – especially the mores socially inexperienced – may assume a greater level of interest than you actually have; some guys take a woman asking him out or making the first move as a sign that said woman is under his sexual thrall and they’re off to make 30 minutes of squishy noises any minute now. But hey, if that happens… well, it’s one of the risks of putting yourself out there.

And if he turns out to be one of those idiots who is threatened by the slightest alteration in traditional gender roles, then really, you’re better off not dating him, aren’t you?

Go ask out some cute nerdboys. You’ll be glad you did.

DEAR DR. NERDLOVE: was wondering if you could help me with a problem. I know most people write to you asking how to get OUT of the friend zone, but I’d like your advice on getting INTO it. Allow me to elaborate:

There’s this girl at work who likes me, but I don’t share her feelings. She wants to go out with me, but I’m really not interested in a relationship. It’s not like there’s any problem with her. Simply put; she’s in MY friend zone.

I met her at work. The company I work for was preparing to open a new branch near my job site, so they hired a bunch of new trainees. She was one of the new people me and my coworkers helped to train.

She apparently took an interest in me because I’m bilingual and she studies foreign languages, which was nothing new for me because I’ve had numerous coworkers who study foreign languages and they’re always interested. I gave her the standard carbon copy routine I give everyone who ever asked about my language skills: Yes, I’ve lived overseas. Yes, most of my family is bilingual too. Yes, I sometimes dream in two languages. Yes, I can watch foreign movies without subtitles. No, I can’t think in one language and speak in another. Etc. Etc.

At one point she asked if I’ve ever had a foreign language job, and I mentioned that I regularly write for a foreign language website. Shortly after that, she found my twitter account on the website and began asking questions about my experiences via twitter after she started working at the new branch. 

Over the next month, she would often ask about me, my hobbies, and things like that. I kind of got a hint that she liked me but I wasn’t completely sure until today when I ran into her and she abruptly asked me if I wanted to go out for dinner some time. I was kind of caught off guard at the moment and sort of mumbled, “Yeah, sure.” and watched her half-walk, half-skip away. Now I feel like a total douche because I realized that since I feel no romantic attraction to this girl, if I don’t do something, I’ll be stringing her along like the so many girls I pursued back in high school who I’d follow like an obedient little puppy. At the same time, I don’t want to hurt her. I don’t dislike her or anything. It’s just that I don’t feel any romantic emotions for her. She is, to repeat my earlier statement, in my friend zone.

I don’t know what to do here. I’ve spent all my life chasing after girls, I don’t know how to deal with being on the opposite side. How can I get her to stop liking me without hurting her?

On another note, do you have any idea why she started liking me to begin with? I treated her the same as I did all the other trainees, I don’t recall ever sending any overt signals that I was interested in her, I even told her about my geek hobbies (computers, movies, anime, and a video game collection that could choke a whale) when she asked, which up until now would usually send girls packing. Where did I go right, the one time I didn’t mean to?

Sincerely, 

Bad Wolf

DEAR BAD WOLF: Well that’s a first. It’s not very often we hear from a guy trying to figure out how to let a girl know he’s not interested.

First things first: unfortunately, there is no guaranteed painless way to let someone know you’re not interested. If there were, we wouldn’t have an entire genre of music devoted to “I Love You Why Won’t You Return My Feelings?”

On the other hand, we’d be getting rid of at least 90% of Taylor Swift’s career. So, mixed bag.

The best thing you can do is be short and direct: tell her you’re flattered, but you’re just not into her that way. It’ll suck for her, but the clean break heals fastest and shows respect for her by not dragging it out or stringing her along.

Now as for why she’s into you: you’re her superior, which means you are essentially a leader and many women find that attractive. You treat her like the other trainees, which can be seen as confidence. Also:  you’re exotic to her. You’ve lived an interesting life – you’ve lived overseas, you speak two languages fluently, you have a job that entails writing in your non-native language… these are all things that set you apart from just about everybody she’s used to. If you’re into anime, you’ve undoubtedly seen the trope of the transfer student who used to live abroad and came back home more worldly and experienced than his peers.

Guess what, BW? That’s you. And she’s the giggly classmate with a crush.

You’ve done things she’s never done, seen things she’s never seen… all of this can make someone quite the dashing figure. Hell, she may well have dreams of living abroad herself one day… and here you are, a living example of her goal.

Long story short, you’ve demonstrated a host of qualities that women find attractive, you just didn’t realize you were doing it. Keep this in mind for next time you’re interested in someone else: you have a lot more going for you than you give yourself credit for.

Oh, and quit treating being a geek like it’s a bad thing. Lots of women are into geeky dudes. Just ask Shrinking Violet up there.

Good luck.

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