DEAR DR. NERDLOVE: I met one of my best friends in elementary school– he used to be my worst enemy, actually, in that I-will-hate-you-forever kind of way. However, during middle school, we started becoming more friends than enemies, and now we’re both in high school and we have a solid friendship. (We initially bonded over arguments about everything in the nerd spectrum, actually… and still kind of do.)

The problem is that he has a BIG HONKING UNREQUITED CRUSH. On me.

And I don’t want to date him.

The problem is that, ever since we were really little, the entirety of the universe has proclaimed that We Would Make A Cute Couple. Both sets of parents. Pretty much all of our friends, even some of the ones that I have explicitly told “NO I DO NOT WANT TO DATE HIM.” When we were little, both of us said it about the other repeatedly (said crush of his had not, presumably, been in effect by then). I’ve said it in front of him numerous times. When he was little, he said it in front of me numerous times. I continue to say it whenever some of our friends corner us. I say that no, he’s my friend and a nice guy, but I’m not looking for a date right now. Clearly, seriously, politely, and using those exact words.

He, on the other hand, mostly changes the subject.

I’m trying to be nice, but it’s gotten to the point where I’m hitting this guy over the head with it and he’s still doing a lot of things that I don’t want him to do. For example, he’s gotten into the habit of trying to drape himself all over me, like an octopus or a stage curtain. I let it slide the first time because I wasn’t really aware of his BIG HONKING UNREQUITED CRUSH, but then he thought it was OK all the time. Later on I started to shy away from his Yawn-And-Stretch Maneuver arms, as well as pointing it out whenever he tried to do it again (“Dude, you are acting like a possessive octopus.” “Please realize that this should be completely platonic.”) and I thought he finally got the point after it tapered off a little.

Until recently, when he asked if I would like to hold hands with him. I told him no.

“But–”

“Nope. Sorry.”

(whiny) “Aww, why don’t you just give in?”

This, in particular, set off a Giant Red Flag for me. I told him no, seriously, twice and he then tried to somehow persuade me into holding hands with him??? (For the record: he is not a touchy-feely person with his other friends and I haven’t ever seen him hold hands with any of his other friends.) Please stop it, Friend with Crush. 

How do I get this guy to get the point that no I do not want to date him? I have basically hit him over the head with it, but he won’t stop trying. 

— Gamer Girl Needs a Break!

DEAR GAMER GIRL NEEDS A BREAK: You know, there are times I really regret talking about how to escape the Friend Zone.

(Standard disclaimer: There is no “friend zone”. There are just people who don’t want to date you.)

A critical part of trying to make the jump from friend to lover is understanding that sometimes it’s just not going to happen no matter how badly you may want it, and the only thing to do is let it go like a goddamn adult. Unfortunately, there are people who insist on pushing and pushing and pushing and then complain to me when they’ve ended up alienating their friend entirely. 

Case in point: your buddy, GGNaB. This is a guy who doesn’t get it and you need to crack a clue-by-four over his head. Repeatedly if necessary.

You can start by establishing some boundaries. From the sounds of things and the examples you’ve given me, you’ve been trying to be as polite about telling him to back off with out actually saying the words “Back the hell off” and making them stick. You need to draw a very clear line in the sand, not just with the Octopus, but with his cheer squad as well and be ready to enforce it.

Here’s what you say:

“I don’t want to date you. I am not attracted to you, I have not ever been attracted to you, I’m not going to be attracted to you and I need you to stop trying. I don’t appreciate it when you start trying to get physical with me, I REALLY don’t appreciate it when you don’t take ‘no’ for an answer and to be perfectly honest, you are making it hard for me to want to stay friends with you. Either you build yourself a bridge and get over me, or we’re not going to be friends any more because it’s not fair to me that you keep making ‘why won’t I date you’ a condition of our being friends.”

That is the end of the discussion. Don’t let him whine, debate, derail or otherwise try to get you to soften your position because there’s nothing else that needs to be said. Repeat “I’m not interested in discussing this any further” and walk the hell away if he insists on continuing. 

You’re already seeing someone with some serious boundary issues – continually doing the “oh I’m just going to drape my arm around you because we’re friends (please accept my boner)” or asking you to “give in” (ugh) and if you don’t shut him down hard, then things are only going to get worse. The more you let him get away with without comment or pushback, the more he will be seeing this as tacit permission to continue.

This means that you need to be willing to act on your ultimatum. If you tell him that you’ll cut him off and don’t follow through, it’s only going to tell him that you’re not serious and that he’s got another chance to wear you down.

If he can’t get past his crush enough to act like a grown-ass man, then he’s proving that he’s not really your friend. If he doesn’t care enough about your comfort or your wishes, then you need to be willing to cut ties. It’s not fair that your friendship has to come with a side of aggravation and clingy, needy BS.

The same goes with all of your friends. You need to be willing to stand up for Team You and tell everybody else that either they can get with the program or they can back the hell off.

Hopefully this will be the wake-up call that your friend needs to straighten the hell up and move on. Otherwise, it’s time to dump him.

Good luck.

DEAR DR. NERDLOVE: I’m delving a bit in my past here, not because it still hurts me (not anymore its been awhile) but because I want to figure out what kind of situation it was and how it potentially happened.

I’ve been watching your videos on YouTube about “Nice Guys” and although it’s different, I think I may have acted a bit like a Nice Guy… even though I either tell the girls I like them, or just don’t go through with it and get over it.

But me and the this one particular girl, we were just friends, and it was like best mates (I’m from the UK). There was a two year difference but it wasn’t a problem, plus she had a boyfriend who I am still friendly with. But one day their relationship started to sour and eventually they split up, but I didn’t take advantage of it because I’m a bit weary of younger girls anyway and I didn’t fancy her.

The last I saw her properly was a few years ago I think, and for some reason not only did she split away from him but also drifted away from me for no apparent reason. I did get a bit worried because she did have other problems (I only talked to her about it, I didn’t want to get involved in any of it though). It didn’t help that she only communicated through a mutual friend and was using words like “back off” and “give me space”, which in my limited knowledge is something your partner says, and we were just best mates, borderline platonic.

Now I do admit at some point I thought I had a crush on her, but I didn’t and I’m glad I realized it was platonic because I had never had that relationship before so i didn’t now what it was.

Anyway after that she just cut off all communication, I did ring her a few times but no answer. I never knew what made her end our friendship considering the great times we had, I was kinda depressed about it for quite a while for some reason, it was kinda like losing a partner but worse because this is a girl who is the sister I always wanted in a way! So I thought of what she might have done to me, like maybe she was being depressed too, or bitchy or I don’t know. Maybe I was being full on? I don’t know. I just want to know what kinda situation this is, cos it has only really happened once and its puzzled me for ages! Literally I have never heard anything from her since.

Help?

Confused Ex Friend

DEAR CONFUSED EX-FRIEND: So you’re a good example of what the previous letter was talking about, which means in this case that you’re going to be something of a warning to others. You had a friend who was trying hard to establish some boundaries and - when you didn’t listen - cut you off entirely.

Here’s a hint: when someone says “back off” or “give me space”, you back off and give them space. Doesn’t matter that you weren’t dating; not having sloppy-makeout privileges doesn’t grant you immunity from respecting someone’s boundaries. This is especially true if she’s gone so far as to have somebody else doing all of the communication. She made made it very clear what she needed from you. You chose to ignore that and, well, you can see what happened.

Why did she drift away from you after her break up? Who knows. Maybe they divvied up the social circle and he got you while she got someone else. Maybe she associated you with bad memories of that relationship. Maybe she just really needed some time to hermit up and heal on her own terms. You’re not going to know, and the best thing you can do is make peace with the fact that sometimes there are no easy, clean-cut answers.

It sucks that things ended like that and you lost a friend, but now at least you know to do better the next time.

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 recently met this girl at a Halloween party, we hit it off and I ended up making out with her before she left the party. So far so good. The next day, not wanting to repeat the mistakes of the past of being unclear with my intentions sent the following message

“Hey,

So I’ll be honest, I don’t know what last night was, but I enjoyed it and I’d like to do it again. So do you wanna get coffee or see a movie sometime, see where it goes?”

She said yes and I ended up hanging out at her place to watch a movie. We talked some more, it was awkward at first but things seemed to be going well. I learned that she was 3 years older than me (she’s 24, I just turned 21) but that didn’t bother me, I’d had bad experiences dating people younger than me in the past and thought this would be a nice change of pace.

This time we hung out also seemed to go well, we made out on her couch, almost had sex but stopped cause her sister was coming over soon and she didn’t want to be caught in the act. No biggie, fair enough. We leave it with her giving me a lift home and making out in her car and agreeing to see each other again soon. So she goes away for the weekend to see her other sister and I go down to Melbourne for my birthday. I try messaging her over the weekend once or twice but she doesn’t respond. I don’t even get a text on my birthday from her which is the least i was expecting. I get back to town and send her a message to see if she wants to hang out. She says she’s babysitting her sister who is in town for work experience, also, no problem. I say “Hey, that’s ok, doesn’t mean we can’t talk right?”  

Then get this message from her:

“Hey, sorry I think you might have got the wrong idea when we met, I just want to be friends, I just thought I’d let you know”

Am I right to be confused? Being ‘just friends’ is certainly not the impression I’ve gotten and I don’t know how to move forward from this. I haven’t had the best luck with women and it’s been 3 years since my last and first girlfriend.

This is the message I sent afterwards which she hasn’t responded to

“Well you can see how I might have got the wrong idea. All I know is that I’ve liked hanging out with you the few times I have, and it felt to me like you did as well. I know jumping into something, whatever that might be can seem daunting but it doesn’t have to be.”

What should I do?

Heartbroken In the Outback

DEAR HEARTBROKEN IN THE OUTBACK: I hate to be the one to say this, but you need to accept that you got rejected and move on.

Here’s what happened:

She was cool with making out with you at the party. She liked you well enough to give a shot hanging out with you and making out some more when you hung out at her place. But then once she had some time and distance… well, she decided she wasn’t so into you after all. It’s hard to say just what flipped that particular switch; maybe your messaging her over the weekend struck her as being needy or clingy. Maybe she was seeing someone else casually at the same time and decided to get serious with them. Maybe she rekindled things with an ex. Maybe you were some naughty fun on the side when she and her significant other were on the rocks. Maybe her sister went all Iago on you and changed her mind.

Or maybe she just decided out of the clear blue sky that you weren’t her type, sloppy make-outs aside. That also happens.

But regardless, it happened and she was trying to give you the wave-off. First, she didn’t respond to any of your texts. As I’m always saying: one unanswered text is happenstance. Twice is worrysome. Three times is a message. No response is a response, after all. When you were back in town and continuing to not pick up what she was laying down, she gave you a more overt “no” by giving you the LJBF speech.

Now it might have been nice if she was more upfront – it would’ve saved you some heartache and her some annoyance – but unfortunately, it happens and you can blame society for this one. As I’ve said many times before: women, even in the 21st century, are socialized to be indirect when it comes to turning men down. They’re taught that they should be as solicitous of men’s feelings – even to the point of sacrificing their own – and as a result, frequently couch rejection in softer terms like “I just want to be friends” or “I’m not in a good place for a relationship right now”. What they mean is no, but saying “no” directly is frequently a risk – occasionally a physical one when the men take things badly.

To be fair: her framing things as “I think you might have gotten the wrong idea” when you’ve had repeated make-out sessions is pretty disingenuous. It absolves her from any part she played in your hook-ups (because I’m assuming this wasn’t because one or both of you weren’t so sloppy drunk that you couldn’t consent… right?) because how could you not see that she was sucking face in a totally platonic fashion? Maybe you missed her mentioning that she wasn’t looking for a serious thing? Dunno, I wasn’t there. And in the end, it doesn’t matter.

You had some fun times, they didn’t last as long as you would’ve hoped. It sucks, but there’s really not much to do but pick yourself up, dust yourself off and move on to the next make-out session.

Good luck.

DEAR DR. NERDLOVE: Long time reader but first time really asking a question. When do you just ask the girl out? When do you decide to ask? I’m not afraid to ask I just never know when to ask.

My example is last night, I went to my coworker’s last day karaoke party and gender imbalance is a bit high. It was only her and 6 dudes but her friend stopped by. We have a good time singing and I occasionally talk to her lady friend. Eventually we actually do start having a conversation. We flirt, we talk I even set up this whole thing where the rest of the night her goal is to get another $1 so I’ll exchange one of my $2 bills with her. It’s playful and fun.

Of course sometimes we split apart for a bit sometimes. I have to go a bathroom, I’m talking to someone else, she wants talk to my coworker who she’s friends with. Whatever. But she decides to bail early at the exit of the next bar. Now, I realize I could have just asked her for her number right here but I’m not so courageous that I could ask in front of all my coworkers. Maybe this the problem? But I’m not really sure how to ever set up the asking. Am I putting too much emphasis on the actual asking? Should I just stop giving a crap about being rejected in front of people? Should I just work it in the conversation earlier?

Any advice would be much appreciated.

Biting The Bullet

DEAR BITING THE BULLET: Don’t overthink things. If you’re having fun, tell her that you’re having fun and you’d like to see her again. When in doubt, you can always pre-seed a potential date by bringing up an event that you’re looking forward to, then inviting her to come with you later on in the evening.

As for the “asking her out in front of people” issue: don’t sweat it. Most people aren’t paying attention to your conversation, and even fewer are going to notice and/or care that you’ve asked someone out. Same applies if she turns you down; as long as you don’t make a giant production out of it, then nobody else will either.

If she says no, you smile, shrug, and say “ok, cool, thought I’d ask” and then change the subject like it’s no big deal. If you’re especially nervous about doing this in front of people – and can’t find an excuse to get some air together or get a drink or what-have-you – then just create some intimate space by physically positioning yourself with your back to the rest of the group as you talk to her. Instant social privacy.

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 been reading the advice you’ve been giving many nerds like myself and I must say it is truly great. I come to you today with a problem that I feel is so simple to resolve but I just can’t see the solution (or maybe I don’t want to). Anyways I just turned 33 and moved from Kentucky to Los Angeles to begin film school in September. In my first class (classes are 1 month long) I had a group project to do. In my group was this girl who I thought was attractive but other than that I didn’t give her much thought. Then we got to talking and things started to change.

The first thing was that I felt as though we had a lot in common. Now of course both being in film school this was probably to be expected. However it wasn’t just that we both loved movies or anything that simple. We basically had extremely similar viewpoints when it came to film. Name a movie we had both seen and our opinions would totally agree with each other. In the beginning I just chalked this up to happenstance. Like I said earlier, people in the same fields generally have the same interests.

Anyways we are working on our projects and sometimes we would give each other a look when other people were dragging things along. She then proceeds to make the comment about how we can communicate with each other through nothing but our looks. (For the record she understood what I was saying way more than I understood what she was).

At this point I started to wonder if she liked me but wasn’t sure. None the less I began to playfully tease her and what not. Well that class ends and we have the weekend off before starting a new class together on the following Monday. Before we go any further I feel that I should mention that she is 22 and lives about 3 hours away, two things I took into consideration as to whether or not she wants a relationship with me.

So class begins Monday and she texts me about where the classroom is. This wasn’t the entirety of our text conversation though as we made a few jokes back and forth. Between classes on Monday, we went with some other people to get lunch but we sat together, with one other person. On Tuesday I took a seat next to her in class. She sent me a funny text about the class, I replied and then I asked her what she was doing for lunch that day. When lunch time came she decided to go hang out in her car and I went to get food.

These last few days we have said simple hellos and what not. I’m trying to not crowd her or come off as a creeper. I’ve sort of felt as though she is trying to distance herself but she isn’t acting differently so that might just be my own insecurities. I also get a little jealous when she talks to other people but I know that’s stupid.

I honestly just don’t know what’s going on. One moment I think that perhaps she does “like” me and the next I begin to wonder if it’s just wishful thinking on my part. I’m also torn because we are going to be in the same classes together for the next 16 months and I don’t want to alienate her or anything because we tend to work well together on projects and such. There’s also the fact that we could very well be work colleagues on day. On the other hand though if she is interested I’d definitely like to give it a shot.

Do you think it’s worth it? Is it possible that she likes me or am I just reading too much into nothing? If I asked her out and she said no would things become weird between us?

Thanks for reading,

Mr. Confused

DEAR MR. CONFUSED: Time to get out of your head, Mr. Confused. You’re overthinking things.

One of the biggest mistakes a lot of people make when it comes to gauging people’s interest is that they spend far too much time trying to read the tea leaves and not enough time actually doing something. It’s totally understandable; you – like many other men – are wanting to avoid an awkward scene where you ask someone out, they say no and suddenly you can’t look them in the eye and everybody’s uncomfortable and you’re wondering whether you need to go to another school.

The problem is that while watching for signs of interest is good, analyzing their behavior like it’s the Zapruder film and you’re trying to prove there was a second gunman isn’t. In fact, most of the time, that’s a procrastination tactic. You’re fooling yourself into thinking you’re actually making progress by doing research when in reality, all you’re doing is spinning your wheels. The problem is that, in dating as in life, fortune favors the bold and the active. The longer you hesitate in asking somebody out on a date, the more lessen the chances that they’re going to say “yes”. Let us start from an optimistic place and assume that she digs you. The longer you wait to ask her out on a date, the message you’re sending is that you aren’t interested in them. Meanwhile, while you’re hemming and hawwing, other people who don’t hesitate are asking her out. Even if she does like you, you haven’t sent any signals or made any moves. So whether she likes you or not, the fact is that you’re not doing anything and other folks are and the odds are that she’ll take the bird in the hand vs. the one in the bush (as it were.)

Then there’s the fact that delaying and procrastinating means that you end up bleeding off the attraction you do have. Hesitation and hoping for others to do the heavy lifting for you isn’t a great look on most people and that initial “ooh, this could be fun” can vanish if you’re not careful.

(Yes, it’d be great if more women made the first move. Unfortunately, gender roles are a bastard and society tends to punish women for being forward. So while we all should work towards a more socially equitable society where everyone feels equally empowered to approach, we also have to deal with the situation as it stands on the ground.)

The other issue is, honestly, most of the time when guys are reading the tea leaves, they already know what the answer is, they just don’t want to hear it. So they spend a lot of time looking for reasons why they’re wrong instead of just accepting that it’s not going to happen.

So what’s going on in your case? Well, it could be that she liked having a classroom buddy to make jokes with and dialed things back when she sensed you were interested in taking things to a more personal level. Or it could just be you’re in an intense program and she’s got her own things going on that have absolutely nothing to do with you.

But the easiest way to resolve this conundrum? Ask her out on a date. Say “hey, I have a lot of fun hanging out with you in class, and I’d love to take you out on a proper date. Would you be interested in doing $COOL_THING this weekend?” Either way, it solves your dilemma. If she says yes, then you’ve got a date. If she says no, then you’ll have your answer and be free to pursue someone who is interested in you. Either way, it actually moves you forward instead of leaving you stuck in this limbo where nothing is happening and you’re just building up more anxiety for no good reason.

You know how you keep it from being awkward if she says no? Don’t make it awkward. Getting turned down for a date isn’t anything to be embarrassed over or to treat as something shameful; it only becomes awkward if someone behaves awkwardly. If she says “no”, then you say “OK, not a problem. See you in class tomorrow” and just behave the same as you have been before. It only gets awkward if you treat her refusal like something shameful or a personal insult; if you suddenly can’t meet her eyes or refuse to talk to her afterwards, then, yeah, it’s gonna be awkward. On the other hand, if you treat her the same as you did before you asked her out? She’ll see that you’re a cool, well-adjusted guy and there’s no reason to feel uncomfortable around you. Most people are going to follow your lead when it comes to potential awkwardness; if you don’t treat it like a big deal, then they won’t treat it like a big deal.

Good luck.

DEAR DR. NERDLOVE: I’m a big fan of your blog, and as I find myself trading fairly new romantic ground, I wanted to ask you for advice.

I consider myself something of a loner, partly by choice and partly because I’m somewhat eccentric. I’m friendly to the people around me, but I infrequently reach out to them. Recently, however, a cute girl in one of my longer classes actually asked me out. I said yes out of curiosity, and to my surprise, when we went out for beers the next day we totally hit it off.

We’ve been dating for a week now (I know, barely any time at all), with things intensifying quickly emotionally (but no sex yet). She’s recently out of a 3 year relationship, and I’ve been off the dating circuit for… almost as long. But I’m having a great time. The thing is, she’s the kind of person who’s super intense and stays busy practically all the time. I, on the other hand, am a laid back geeky slacker type of person, who dislikes planning things in advance and spends plenty of time loafing around.

Therein lies the problem. When I try to make plans with her, I find invariably that she’s made tons of previous commitments while I’m almost always wide open. I’ve ruined previous relationships by being overly clingy, so I’m very conscious of the image I’m projecting here: that I’m always available, that I don’t value my own time, etcetera. What’s the best way to setup a date without seeming like somebody who doesn’t do anything with his life (which I… kind of am)?

Thanks,

Probably Needs to Do More Stuff

DEAR PROBABLY NEEDS TO DO MORE STUFF:

This is simple, PNDMS: you use your words. Instead of worrying about the image you’re projecting, just ask her what her schedule is like.  Say “Hey, I’d like to do this thing with you; when will you be free?” and find a time when she’s available to go on a date with you. You knew what her schedule was like when you started seeing her. You may not like making plans in advance, but that’s going to be part of the price of entry when it comes to dating her. So you’re going to have to learn to roll with it if you want this to work.

And while I get the fear of being clingy, there’s a difference between being a needy ball of slop and having more free time than the other person you’re seeing. One is about constantly trying to occupy her time because you’re afraid she’ll not like you if she has a few minutes to think about it and the other is simply lifestyle differences. Having a more flexible schedule doesn’t make you needy; constantly badgering her for dates or saying “how about tomorrow? Ok, the day after that? OK, the day after that?” on the other hand, is. It’s VERY early days yet and you can’t reasonably expect her to always move heaven and earth to see you when you want. So for now: you propose the date, she proposes the time.

Good luck.

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