How Do You Date Casually Without Leading Someone On? Plus, Distancing Yourself From Cliques


Like anything worth having, relationships and friendships are both difficult to develop and to maintain. Your questions this week exemplified that. However, whether you’re trying to meet the Paul to your John or the Yoko (ugh) to your John, remember to be mindful and to avoid mind games.

Send us more qUeStIoNs for next week’s mailbag (in the form below). Or selfies!

– Steph and Lance

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Q: I’ve been single since May for the first time in a 2 years. I’ve finally gotten over everything and now I’m ready to get back out there. I’ve had classes with him for years and I’ve always though he was really cute. This semester, I have two classes with him and we’ve been talking a little bit. He also sits next to me in one of them! He’s really shy and I can be a little shy too sometimes. But I’m also not the type of person to wait around for something to happen on its own. I want to ask him out, but I don’t want to freak him out. We haven’t exchanged numbers or anything and I’m not sure how to initiate this, how to ask him out, or even what I should ask him to do (dinner/coffee/etc). Do guys like it when girls ask them out or does it come across as desperate?

Lance: If you’re the go getta that you say you are, it’s definitely a good move; it’s intriguing, it’s different — flipping norms on their head is always attractive in a relationship, because it makes your relationship/courtship seem unique. That in itself is incredibly attractive.

The key though, if you’re looking for something a little bit longer term, is to make sure that you retreat at some point. Pull him in, see that he’s really invested, and then take an emotional step back. This where you initiate the traditional “chase,” and it’s where you’ll really get him. In the two “girl chases guy” things I experienced, one pulled that off really impressively. When things eventually fell apart, it took me a bit to recover.

Steph: Asking people out is daunting.

That being said, I think you should just go for it. You have nothing to lose because the worst that can happen is that he declines and class becomes marginally awkwarder for a week or two.

It might be easier to start slow. Coffee or dinner could be a bit ambitious, especially if you two haven’t hung out before outside of class and because they are such contrived social interactions. It could scare him off if one day after class, you go up to him and randomly ask if he wants to get dinner. Wide-eyed enthusiasm isn’t cute in all situations.

Before you go that far, ask him if he wants to study with you or work on a problem set together. See how that goes first and add ‘za later.

Q: I’ve always wanted JUST TWO FRIENDS. Just two. My mom says that’s wrong of me and that I should have a group of people to hangout with and not to “limit myself.” Recently this “group” more like “clique” I’ve been hanging out with has started to become catty and competitive in many different ways. How do I get out and is it okay to just want less friends…

Lance: The reason that cliques exist is so that there’s enough people in the group to make gossip about behind their backs without them finding out. (And if they do find out, they can’t say anything because they’ve certainly been doing the same thing.) You can’t pull this off with two or three people, because the pool of flawed humans is simply too small.*

*This probably wasn’t helpful at all, but just know that if you feel the need to criticize the clique at every turn, you are far from a bad person.

Steph: Cliques are inane, and once you’re past a certain age, they serve no purpose other than ensuring that you have a solid circle of people in your life who will “like” all your recent Facebook activity and hold your hair in case you need to, say, puke in the bathroom of a Steak ‘n Shake.

The number of friends you have doesn’t matter. What does matter is that you feel as though your relationships with them is meaningful. If your friendships have become more of a hindrance to you than anything else, it’s okay to slowly cut ties and search elsewhere for new buds.

What’s that one Drake lyric? Oh yeah…”F*ck a fake friend…where my real friends at?” Keep that in mind.

Q: I’m a 20 year old woman, who’s never dated anyone, a virgin and don’t have any real friends. I’m still in university but haven’t met anyone I actually want to spend time with, friend or boy wise. I honestly think I have ‘undateable’ invisibly tattooed on my forehead. For some reason guys never want to get to know me, or hang out with me or date me. I’ve had my fair share of making the first move, trust me. I’ve given a crush my phone number via a homemade Christmas card, talked to guys on Facebook, done the cutesy stuff, and still, nothing. Maybe I’m just not interesting, maybe I’m to sarcastic. I think I’m great just the way I am and that no guy can handle my wit. The struggle is real. Whenever I go on a trip its always my sister, her boyfriend and I. I’m always a third wheel and am so used to it. Plus my 21st birthday is coming up this June and I want to do something crazy! With lack of real friends, whats a girl to do? Whats your secret to meeting awesome people? I’ve done the clubs thing, students council and alot that I’m passionate about but I honestly find that girls only care about getting with a guy and finding love, that real friends are hard to find for that reason.

Lance: Unfortunately I can’t speak to much of the friend part, as I am a guy, and being friends with other guys is merely a function of both liking food.

The rule of all relationships, though, is that they come when you least expect them to. So for your 21st birthday, I would simply focus on having as much fun as possible. Go out with your sister and boyfriend and don’t worry about anything.

Taking the pressure off of yourself is the most liberating thing a human can do. And ironically, it usually leads to the success you’ve been looking for all along.

Steph: My secret to meeting excellent people (as well as some creepers, along the way) is going up to strangers, striking up a conversation, and telling them about my ongoing obsession with Rocket Power. Okay, so, maybe I keep that little nugget of information to myself, but the point is that I try to put myself as out there as possible — anyone who knows me (and has spent a prolonged amount of time around me) can vouch that I’m a weirdo. But, you know what? I embrace it — or, at least, try to. Do the same, and let your personality speak for itself rather than tailoring it to impress anyone in particular. #Deep friendships will follow.

As for your 21st, go HAM. Listen to Lance: go out with your sister and her boyfriend and don’t fret about being a third wheel — it’s your day.

Q: How do you casually date without leading someone on? Whenever I start dating someone, I feel like they want things to get serious, and I don’t. Any suggestions for letting someone down easy? If you’ve gone on a few dates with someone and nothing about them is awful, but nothing’s all that great either, how can you end it without being a bitch?

Lance: Use the “I’m not looking for a serious relationship” card. The key here is to be as safe as possible in terms of your reasoning, so in the case that you do end up getting back together, you don’t have to keep up the Seinfeldian facade of a fictitious boyfriend that you’ve been having trouble getting over for years.

If you’re in #postgradlife, it’s always a good move to play the “I’m thinking about moving to Boston” card — we are very transient at this time of life, and that excuse will always work. The only time it won’t work is if you are in grad school, in which case you could simply pretend that you need to devote all of your time to studying.

Steph: Most people slowly distance themselves. Calls, texts, and messages become increasingly infrequent until they stop altogether. I’ve done this to people. People have done this to me. It doesn’t feel great on either end. Like Lance suggested, honesty is prime here. Be very clear about what you want and make sure that you know what they want. If your relationship objectives don’t mesh well with theirs, y’all will know to cut your losses and move on.

Additionally, there is nothing wrong with ending a relationship because you don’t feel a spark with someone. You can’t force a connection (if that were true, James Franco would be MINE). You’ll know it when you feel it.