Ask Dr. Nerdlove by Harris O'Malley

How Do I Find Out if My Crush Dates Men?

DEAR DR. NERDLOVE: My best friend works at a games store. I visit her about twice a week in between days I have class to bring her food and keep her company when there’s low foot traffic. A couple weeks ago, I met one of her coworkers, who she’s talked about quite a bit. I’ll be honest, I was judgy and expected to not like this guy based on her description. She made him out to be a very extroverted person and that isn’t the sort of person I mesh well with. But this guy. He’s incredibly attractive and very funny. And he’s genuinely nice! My interactions with him have been limited, but there’s definitely the beginnings of a crush brewing. I mentioned to my friend that I thought he was cute and she immediately prattled off a list of reasons why he’s so great. Damn.

In the past month or so, I’ve unpacked a lot of my own emotional issues related to some past heartbreak. I feel now that I’m better equipped to try and seek out a relationship. But I’m not sure whether it’d be smart to take the risk on this guy. My friend told me that, although she’s only known him to date girls, everyone else at the store suspects that he isn’t straight. I myself am a bi guy, so that should be good news. But the uncertainty is terrifying. The thought of just straight-up asking this guy if he likes guys petrifies me. Another friend suggested I just ask him out and see if he says yes. That’s out too.

If I were to do either of those things, I’d want to get to know him better first, but I’m hesitant. I haven’t gone through the trials and tribulations of getting to know someone and then asking them out in a very long time, and I’m frankly scared to do so. I’ve had my heart broken too many times to count, and I’m just now coming back from it. Am I just setting myself up for that again by thinking of pursuing my interest in this guy? Is it worth the risk?


Cryin’ Bi

DEAR CRYIN’ BI: There’s no reward without risk CB. No matter who you are, no matter what your circumstances, there’s never going to be a point where you can date someone without the risk of pain or disappointment. Whether it’s the pain of being rejected, the pain of being into somebody who isn’t as into you, the pain of breaking up or what-have-you, there’s always the chance of getting hurt. There’s no getting around that.

The key, then, is to decide whether or not that risk is worth it.

Now that doesn’t mean that pain is inevitable, nor does it mean that all pain is equal. Just as we can manage our odds when we play blackjack, we can manage the potential pain of rejection. Part of that is very simple: don’t f

k around and invest so much in somebody you don’t know that you give them the power to destroy you if they turn you down. One of the ways folks end up screwing themselves is that they spend time trying to maximize their chances of getting a “yes” when they ask someone out without actually getting around doing the asking. Before long, they’re so emotionally invested in that person that they don’t dare ask for fear that they’d be turned down and have all their dreams be destroyed.

On the other hand, asking them early means that if you do get turned down… well, it kinda stings, but it ain’t that bad. You’ll likely get over it within the span of time it takes to get a beer, if not sooner.

So, like ripping off a bandage, it’s best done early, quickly and in one smooth motion. As a general rule, I’m a big believer in the Just Ask Him Out, Already approach. By asking someone out on an unambiguous date – not to “hang out some time”, not to “get together” but an actual date – you find out whether they’re into you or not and get a date at the same time if they are. Waiting around “until the time is right” or “until you know for sure” or “know him better” tends to just up the stakes until they’re so high that you don’t dare risk it.

Now that having been said: the fact that you’re bi and you don’t know if this guy is into men means that there’s some legitimate risk here. Plenty of LGBTQ folks, as well as straight women, have been on the receiving end of full-scale freak-outs from sh

ty people, ranging from yelling to outright assault. That’s a legitimate reason to be cautious. But I’m assuming that your BFF knows this guy well enough to know whether he’s the kind of person who’d lose his s

t at a man flirting with him or if he’s the sort of person who would take it in stride. So if you want to be a little cautious here, I’d totally understand. You could conceivably try to thread the needle by inviting him into a convo between you and your friend while you talk about dates and boyfriends previous and see what he says. You could try to feel him out through questions, though that has a higher potential for comedic misunderstanding than actual, actionable intel.

Or you could just cowboy up and say “hey, I don’t know if you’re into guys, but if you are, I think you’re kinda awesome and I’d love to take you on a date sometime.”

But even if you don’t necessarily go for this guy, at some point you’re going to have to get back in the pool. And you can either torture yourself by trying to ease in one millimeter at a time… or you can just dive straight in and start splashing around immediately.

Up to you. You know my vote.

Good luck.

DEAR DR. NERDLOVE: I have a question for you. I’m a kinda short, black teenager in high school and this year (junior year) I decided I want to dress in matching clothing and have some style as much as possible.

So basically I’m not a “socially-inept nerd” but I am a sports playing nerd. I can match my clothes but being in style is hard. I would like your tips on style and maybe some of your style. Thanks.

Jumbled-Up Junior

DEAR JUMBLED-UP JUNIOR: My first rule about high-school is: try not to worry too much about high-school. It’s a giant morass of surging hormones, social Darwinism and a whole bunch of proto-sociopaths who’re busily sharpening their metaphorical knives on anyone and everyone around them where the rules of engagement seem to have been written by people who spent twenty to thirty years in the high-security wing of Oz (and I don’t mean they were trying to find ruby slippers for the Wizard).

Now that having been said, high-school is a place for laying the groundwork for who you will become later on. The sooner you master the basics, whether it’s with social interaction or sartorial mastery, the easier you will find that aspect of your life later on when it does start to count: in college.

So with that in mind, I’m going to advise you that you don’t worry too much about your personal style yet. Start off by making sure you have the basics down pat. This means making sure you’re wearing clothes that actually fit rather than trying to hide any flaws you may perceive in layers of clothing.

Next, keep some simple rules in mind:

First: don’t go overboard with flashy clothes; stick to one piece of clothing that’s the centerpiece of your outfit. Everything else should be basic, otherwise you start to make yourself look overly busy. Same with accessories: keep it simple and minimalist. The more attention-grabbing a piece is, whether it’s a hat, jewelry, a flashy watch or what-have-you, the more it’s going to overwhelm everything else. Think of it like a point system; the flashier it is, the more points it’s going to cost, therefore you will have less room for other accessories.

Next: jeans should be the work-horses of your closet; they can work with any outfit, provided they’re good quality and fairly minimalist in design. The more holes or unusual washes (sand-blasted, for example), the less you can do with them. Dark washes are ideal, as they will work with damn near everything you own and can be dressed up or down. And no decorations on the back pockets. The early 00s have many fashion sins to answer for.

Next: The last thing you put on is going to be the first thing people notice. Keep this in mind, especially in the autumn and winter months. Never underestimate the power of a cool jacket.

Regarding geek-oriented clothing: I’m a big fan of keeping displays of nerdery simple and understated. For example: I wear a custom-made Green Lantern ring, but most folks would never notice until they looked carefully at it. Graphic tees reproducing comic covers, movie posters or X-Men fight-scenes tend to be too much; something simple like the S-shield or the symbiote white-on-black Spider-Man logo are iconic and classic, especially when that’s your centerpiece.

When it comes to shoes: I realize some styles, especially hip-hop and streetwear styles prioritize tennis shoes or basketball shoes. Personally, I think athletic shoes are best used for being athletic in order to keep them from wearing out too quickly. Keep some casual shoes for every-day wear, whether they’re Chuck Taylors, Vans, Addidas or what-have you. You also need one pair of shoes that goes with a suit.

Related to that: your belt should match your shoes.

Also: white socks are best for working out. Dark socks work best for every other occasion.

Track suits are for warming up before exercising or lounging around the house when you don’t give a damn who sees you. Period.

You may notice I didn’t say much about style here. This is because style is an extension of who you are and at your age, your identity and archetype is going to be a moving target. This is a good thing; you should be experimenting with different aspects of your personality and identities as you try to find out who you really are. Find styles that speak to you and people who can serve as a fashion role-model. Just don’t try to lock yourself into who you think you should be or let other people tell you who you are.

This is also a good time to start learning how to shop for clothes properly. Start learning to take advantage of sales and where to find discounts. There are also sites that have daily sales and overstock sales that can help you find designer clothes at a fairly sizable discount.

More often than not, when it comes to clothes, you get what you pay for – but that doesn’t mean that you can’t get it for cheaper if you’re smart.

Good luck.

Please send your questions to Dr. NerdLove at his website (; or to his email,