How To Properly Manage A ‘Flirtationship’. Plus, Which Characters On Girls Are The Most Dateable?

Girls: HBO
Girls: HBO


Feelings are difficult to express. Potential rejection is scary. Emotional vulnerability is icky. Given this week’s questions, y’all seemed particularly interested in exploring these topics, and we did our best to figure out as much as possible for y’all. Also, #lolz at whomever sent in that Girls question.

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– Steph and Lance

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Q: I’m a girl with two best friends that are good looking guys. I’ve been hooking up with one of them semi-consistently for the past year, keeping it a secret from our other best friend and almost everyone else we know. In the beginning it was very casual and hot sneaking around and we were able to balance it with still being best friends. After this long it’s gotten to the point where I can’t deny that my feelings for him are really serious, and I’m sick of sneaking around. He used to push towards a real relationship but I denied him so much that I’m worried he’s given up hope on me now. (also our other best friend would be furious) What do I do? Should we end it before it gets messy? Or should I go out on a limb and tell him what I want?

Steph: This question is too #real right now. I think you should tell him what you want. Frank communication is the only way you can keep your relationship (or whatever you’d call it) from becoming unnecessarily messy. I can almost guarantee that he has some sort of feelings for you, especially if he has continued to see you — despite your hesitance in the past to date/whatever him.

Your other friend may get upset, but I don’t doubt that he will eventually get over it — and if he doesn’t, someone needs to drop a dollop or two of Bailey’s in his coffee.

Lance: Nice. If the other best friend hasn’t gotten suspicious/figured it out, impressive work.

My advice would be to come clean, and have a nice mature sit-down. Seems like one of those things where the friend would be very pissed initially, but then eventually get over it, and actually make you all better friends in the long run. Life does that.


Q: After having what seemed like a “flirtation-ship” last summer, I fell hard for my good guy friend. The only drawback: I went away to study abroad for the fall and was never able to pursue my feelings. There wasn’t a single day that went by, when I was abroad, that I didn’t think of him and when I returned, I hoped to pick up where we “left off”. When we did finally see each other after that long semester, I made a comment making it obvious that I liked him and got friend-zoned right away as he mentioned he was also “dating someone”. As of now, I can’t seem to shake those lingering feelings for him and they are stronger than ever. I’m not even quite sure if he actually is dating someone considering he has never mentioned details about another girl and is also studying abroad as well. I’ve hit a wall, it seems. The distance from our semesters abroad has sort of helped me in keeping my emotions in check (in a way). But when he comes back… any ideas?

Steph: He isn’t back yet, so who knows what could happen? It won’t make you feel any better to speculate or put all your hope into the possibility that y’all might become “something” when he does return. Don’t let that possibility keep you from investing yourself in other people if the opportunity to do so arises. You might lose out on getting to know someone great or he might turn out to be a total Schwald. Disaster often strikes when you hold out for someone; call me a cynic, but it’s just not worth it 65.4 % of the time.

Also, I don’t think the Friend Zone actually exists. Shots fired.

Lance: Seems like one of those situations where you’ll be dating other people for like the next six years (when you’re single, he’ll be in a relationship, and vice-versa), and then you’ll eventually get married. Remember that as long as nothing too ridiculous happens, there is a ton of time in life. It’s sad to say, but even marriage isn’t a total sign someone is out of the game forever.

I wouldn’t stress. Don’t hinge on him, but definitely keep tabs. Meaning that when he returns, reach out, but don’t be too aggressive. If has a girlfriend definitely keep your distance, but also be around enough to be like “if I’m still single when you’re done, I’m around.”


Q: I am a female who is interested in a male friend of mine. I really like him and want to ask him if he feels the same way about me, but he’s just so hard to read. He is one of those people who are nice to everyone, and flirty to every woman alive! He is also in denial of any girls liking him unless he hears it from the girl herself. My friends have been supportive of telling me if I never try then I’ll never know, but I need some kind of mutual feeling. My last relationship didn’t end so well and honestly I am a little nervous if this does not end well either. Should I ask him how he feels about me, or is it obvious that he does not feel the same way?

Steph: One of two situations will play out if you tell him how you feel. He could reciprocate your feelings, and then, beautiful things could happen! Or…he could tell you that he doesn’t feel the same way — at which point, you should immediately respond, “Oh, jk…I’m not actuaaaaally interested in you” and spend the next several weeks ignoring his existence.

But, seriously, just tell him how you feel. If you don’t, you’ll constantly wonder what could have happened if you had.

Lance: It depends what you’re looking for. If it’s a simple “I’d want to start hooking up with him and see what happens,” go for it. If you don’t appear to be serious on the outset, he’ll think he’s got nothing to lose/won’t be scared of getting in too deep. Guys will pretty much always go for that, and oftentimes you’ll end up dating for two years.

If it’s clear you want to be more serious, maybe test the waters by going to a concert or something. Or invite him to a party. Give him a sign, see if he bites.


Q: I read you both fairly often and noticed you both watch Girls. Lance, out of the four major characters, who would you most want to date? To hookup with? Steph, same question but for the guys. 

Steph: This is such a HARD question. Ray is attractive — but in a curmudgeonly way. He seems like someone who would know how to give killer shoulder massages and who would remember to pick up your favorite snacks if he happened to go to the grocery store — necessary skills for any long-lasting, healthy relationship. I’d probably #husband Ray, but I would totally hook up with Adam. He’s no good for me, but that Bad Boy Vibe is way too much to ignore.

Lance: Marnie and Marnie. All Marnie everything. I will explain via the following points:

1. I think Shoshanna is pretty attractive, but I’d be exhausted after 30 seconds of talking to her. Also, we’d by way too hip-Jewish together. Our hip Judaism would be off the charts. Too much.

2. Hannah is impossible to have a two-sided conversation with.

3. I can’t handle Jessa.

4. Marnie is attractive.

5. Marnie would constantly drop incredible life gems, like “I love wraps!” or “But what is yoga, really?”

6. Our relationship would be forever preserved though themed photo albums. Thought Catalog Logo Mark

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