Ask Dr. Nerdlove by Harris O'Malley

I Don’t Know How To Tell My Crush I Like Her

DEAR DR. NERDLOVE: I’ve been a big fan of yours for some time and your advice has helped me through some of my dating misadventures of the last few years.

My current issue is probably not too unfamiliar for your readers. I have a big crush on someone. We were casual acquaintances in college, and about 1.25 years ago I asked her to meet up, knowing that I had some interest in her. We’ve been meeting irregularly and getting to know each other. Recently she has been saying how much she enjoys meeting with me and we’ve picked up our text conversations since the lockdown. I know I want to see those as signs she is interested in me in a romantic fashion, but I also know my mind can make any evidence favorable when properly motivated.

Adding to this is my realization thanks to your advice what one of my biggest stumbling blocks is: I’m boring. I have a very hard time being flirtatious or playful with people I like. I get very anxious about crossing boundaries. I’m not very expressive in my speech in the everyday unless I feel comfortable with someone, and being around my crush is the opposite of comfortable, even though I really like her.

Just trying to find a way to show how I feel and express my attraction and hopefully wring a relationship out of this mess.


Tongue Tied

DEAR TONGUE TIED: At the risk of pointing out the obvious TT: you don’t really have a problem here. It sounds to me like your biggest issue is that you’re too caught up in your own head and overthinking things.

One of the mistakes people make is that they tend to assume that there’s only one way to flirt. They see flirting as a specific process, one that looks exactly like, say, George Clooney seducing Jennifer Lopez in Out of Sight or the witty banter of Nick and Nora Charles or the joking style of Will Smith or Ryan Reynolds. In reality, there are as many ways of flirting as there are people. At its core, flirting is simply communicating to somebody that you are attracted to them and like them as more than just a platonic friend. For some people, that means banter and jokes. For others, that means physical touch and connection. For still others, it’s a declaration of interest, telling someone why you like them or how enchanted you are by them.

The way you flirt is going to be as individual as you are, and finding your flirting style simply means finding the way of expressing interest that is most congruent with who you are as a person.

The problem you seem to have is that you don’t believe that your friend could actually like you… all evidence to the contrary. The fact that you met up frequently before the lockdown, that your text conversations have continued since and she’s telling you how much she enjoys seeing you? I mean… I guess she could hire a plane to fly a banner saying “ASK ME OUT, YOU FOOL” over your house if she wanted to be a little more obvious about it, but that might seem a little gauche.

The easiest way to find out if she’s interested is simply ask her out on a date. Now, considering that we’re in the era of social distancing and self-isolation, traditional dates are going to be off the table for a while. But that doesn’t mean that you can’t tell her that you like her, that you’d like to go on a date and see where things go. I recently released a workshop on dating during the COVID-19 pandemic, which you can find over on my YouTube channel. I suggest you check it out; I give a number of ideas for potential dates that you can have via Skype or FaceTime. One date idea that can be fun is to cook a meal together. Set up your laptop or your tablet in the kitchen, open a video chat and the two of you try cooking the same meal… just in your own houses. It’s a way of capturing the feel of preparing a romantic, candlelit dinner together, even if you can’t be there physically. It’s fun, it’s unique and even the potential for mistakes adds to the enjoyment as long as the two of you can laugh it off.

But none of this can happen unless you use your words. They don’t have to be flowery or silly or witty; you just have to make it clear that you like her as more than a friend and want to possibly pursue a relationship. And honestly… I think she’d be very interested in that.

Meanwhile, as a word of advice: part of how you make sure that you don’t cross someone’s boundaries without wracking yourself in anxiety: pay attention to her comfort. If she starts getting uncomfortable, apologize and dial it back. A simple apology and not making the same mistake again will keep you from being a creeper. And if you’re worried that you don’t know whether something is too far — making a flirty or slightly sexual joke, for example — then give her room to decide where the line is. If you metaphorically lean forward 40%, you give her the opportunity to either take it the rest of the way, or to leave things where they are.

Good luck.

DEAR DR. NERDLOVE: Big fan of your work. Really interesting social insights on modern courtship that goes beyond fallacy-riddled generalizations the average internet user is prone to believe and spread around. 

I’m writing this hoping to get some advice from you about this person at work who I’m having a “unique” case of Oneitis on. I say “unique” because all I’m really after is a physical relationship, and not even an exclusive one at that.

Short history; I met her a few years back in a language class I was taking before I entered this new company. She didn’t really stand out then, as she was always tired from work and wasn’t really participating in that class anyway and I was pursuing someone else at the time. That didn’t work out, by the way, and I’m still single up to this day. After that I was surprised to find out we were going into the same company. 

Fast forward a few months later and I was working with her almost everyday. Tried flirting, even spent some after-work time with her and with another friend. After that she was cool enough to clarify that she wasn’t looking for a relationship. That was my first time being active compared to the old style of just hoping fate would hand me a relationship, so I had to deal with the rejection, which in retrospect was not the worst way anyone can reject someone. I got over it, did some introspection, pursued some other interests while still continuing work with her.

That’s when I realized there was little chemistry to make it work as a standard relationship in the first place anyway and I was just intensely curious on what a physical relationship with her would be like because she hits all my major ‘characteristics I’m physically attracted to’. To sum things up bluntly: she makes me really horny. I totally own my desires, even if it all just looks like fodder for the ‘the power of boners are strong’ stereotype. Of course I’m aware this could be something to consult with mental health professionals with but beside wanking off occasionally it’s not getting in the way of work or social interactions. I did stop the flirting after she told me she wasn’t interested and backed off trying to act normal work. Of course, I can’t dismiss the notion I’m only seeing her not as a person, but as someone to be sexual object and that’s just sad for everyone.

What do you think, doc? Is it worth clarifying the relationship I’m interested in or should I let this one go? How do you usually deal with these kinds of desires

Yours truly,

Jalapeño Horndog

DEAR JALAPEÑO HORNDOG: Here’s the thing, JH: if there’s not enough chemistry to make a romantic relationship work, then there’s almost certainly not enough to make a sexual one work. While asexuals and demisexuals certainly exist, it’s a safe assumption that the former is going to come bundled with the latter.

But in this case, there just wasn’t any interest there, period.

If her objection was at having a romantic relationship but she was interested in having a purely physical one with you, she would’ve given you the heads up. “I’m just not looking for a relationship” almost always comes with an unspoken “with you” appended to the end. It’s a softer way of saying that she’s not romantically or sexually attracted to you without being rude or confrontational about it.

Your being attracted to her is perfectly normal. But as I’m often saying: attraction isn’t a commandment. You can be turned on by someone and not do anything about it. You can fantasize about someone all you want, but otherwise you need to let this one go.

Good luck.

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