“i’ve liked this guy for a bit now, but the issue is that he has a girlfriend and lives with her. he’s told me they have issues and i obviously don’t ask anymore about it since it’s his life, and i wouldn’t want to interfere with his relationship. i don’t want to tell him how i feel, because i don’t want to ruin things between us since I enjoy being his friend. what should i do?”

on Jersey Shore, mike “The Situation” told “Snookie” (who was very upset with her boyfriend) that he loved her and that this was evident because of how quickly he answered her text messages. i believe the episode ended with her throwing a bottle of champagne at him. so probably don’t do that.

i can’t speak to whether or not this boy likes you, nor can i give you a series of steps to take that would end with him and you together.

there is a somewhat easy solution, though. just keep being yourself and enjoying life. realistically, one of two things is going on—one, he’s genuinely unhappy with this person and looking to find the strength to end it. or two, he’s just going through a rough patch and the relationship will stand.

if it’s the later, well, you’re being yourself and having fun which is what you should be doing anyway. someone else will come into the picture and things will be hunky dory.

if it’s the former, then by living a fun happy life, you’ll be providing reassurance to him that being single isn’t so scary and that he doesn’t need to cling to someone that doesn’t make him happy just to avoid it.

realistically, you shouldn’t get your hopes up. there is no particularly healthy situation wherein the two of you end up together in the near near future, but life is long. if you guys stay friends, who knows what could happen.

“i can’t stop comparing myself to my ex’s new girlfriend. what should i do?”

look, we’ve all been there. it’s 2:30am, you’re laying in your bed a little tipsy, mindlessly scrolling through Instagram and suddenly you get the brilliant idea to type in that old familiar handle… and guess the fuck what, they’re seeing someone else. Alexa, play Mr. Brightside.

there is no one version of you. you’re a different person when you’re with your mom, when you’re with your best friend, and also with every single romantic partner you’ve ever been with. and—this sentence is going to be a nightmare—every single romantic partner you’ve ever been with will be a different person with every single romantic partner they ever have.

so yeah, maybe your ex seems happy with his new girlfriend. maybe he’s going to spend more time with her than he did with you. maybe he’s finally going to start doing that thing you were trying to get him to do for years and you asked him every fucking day and he never did it and now with this girl he’s going to—it doesn’t matter, though. because, provided this new girl isn’t just a rebound, his new relationship will include a new set of sacrifices and shortcoming—not equal to, greater than, or less than those of your relationship, but different.

understand that this boy never knew you and you never knew him. you each knew the version of each other that the other brought out in you. and his new girlfriend will never know the exact version of him that you knew. and finally, understand that the versions of yourselves that you presented to each other were not compatible with each other.

“when’s the best time to have the “what are we” conversation?”

hanging out with someone new is exciting—especially when it’s someone you really like. asking “what are we?” runs the risk of scaring them away so it can be tempting to put this conversation off. but it’s important, especially at the start of something, to have some kind of conversation about each person’s intentions. however, instead of “what are we?”, you should try asking these two questions.

first, “what are you looking for?” does this person want a relationship (presumably with you) and do they feel they’re in a good place to embark on one. this is a good time to air any (relevant) dirty laundry about ex’s or recent breakups—as well as finding out if they’re seeing anyone else.

if it turns out that this person is interested in or open to someday having a relationship with you (and you with them), it’s then time to talk about what kind of relationship they feel comfortable with. polyamorous, ethnically non-monogamous, and “monogamish” relationships are becoming more and more mainstream and it’s important to clarify what you’re comfortable with in any given situation.

so—now that I’ve completely changed the question—when should you have that first “what are you looking for?” conversation? since this conversation isn’t about what you “are” it can and should happen before you “are” anything. that is to say, the answer is, really, pretty much as soon as you start to feel that you might want some kind of a relationship with this person. after all, “playing it cool” only has the capacity to make this person like the version of you that’s “playing it cool” so unless you want to keep that up for the duration of your relationship, you might as well just be yourself.