Ask Catherine Cohen: How Do I Get My Boyfriend to Dress Better?

Comedian and actress Catherine Cohen has built a cult following for her chronicles of the bizarre, often humiliating experience of being a 20-something woman. In her original show tunes and on her popular podcast Seek Treatment (co-hosted with fellow comedian Pat Regan) she skewers the clichés of millennial aspiration, deadpans about sex on antidepressants, and earnestly celebrates such triumphs as finding love or drinking seven beers. Her first book, God I Feel Modern Tonight: Poems From a Gal About Town is out now. Have a question for Catherine? Send it to askcatherine@wmagazine.com.

Sooo my boyfriend of 6 months has...not good taste in the clothing department. I consider myself a fashionable New Yorker (brag) and I don't need my bf to be, like, an uber-fashion guy, but I just want him to elevate his wardrobe a bit. Do you have suggestions on how I can go about helping in this department without hurting his feelings?

First things first, congrats on the boyfriend—love is, as you know, actually all around™, but it’s still hard to find a man worth talking to and having sex with in this economy! Now to address your question: Let me begin by saying honey, I have been there! The first guy who made me cum wore Hollister from head to toe and since then I’ve had incredible erotic encounters with men who have worn items including but not limited to: cargo shorts, “fun/jokey” socks, skinny jeans, and (drumroll please) a newsboy cap!

Have you talked to your boyf about his relationship to clothing? If you have and he’s totally disinterested or 100% committed to wearing his current wardrobe ’til he passes away, I would leave it alone and instead ask yourself why you care so much. Of all the horrible things men do, dressing sans panache is a minor offense. However, I doubt this is the case. Thanks to society (that sneaky little slut) most men, especially straight men, feel as though the world of fashion has never opened itself up to them.

Have you offered to take your boyfriend on a fun shopping trip? Do you ever find a cute outfit online and say, “Omg I would be so horny towards you if you wore this?” As long as you approach this makeover from a place of confidence and positivity, I bet you can get him excited about upgrading a bit. Show him cool designers you like, tell him how sexy he looks when he tries something new, etc. You get it. Also, as an aside, boys get really excited in Uniqlo (a shoppe that I find sexless and humiliating). But I’ve taken a few lovers there and they really come alive in the space. This isn’t sponsored by Uniqlo, I’ve just found it to be an affordable and approachable starting point for certain clueless men.

At the end of the day (ugh I’ve been watching too much Love Island), I totally understand where you’re coming from. It can be disheartening to watch a hunk not realize their full potential sartorially, but his disinterest in outward appearances might also be one of the reasons you’re drawn to him. What is sexier than not caring? Can you imagine how powerful I would be if I didn’t think about what I looked like 4,000 times a day? Don’t answer that, I don’t want to know!

K, so, we all know that having a crush is literally the only thing that makes life worth living but what do you do when it spirals out of control and consumes your life?? I’m hopelessly in love with my boss (lol) who is completely unattainable (happily married). This crush has grown so gigantically out of control that I’m not even interested in, like, actually attainable people who have expressed interest in me. How do I stop being obsessed with him, especially because I don’t really want to stop being obsessed with him?

Okay, so just to quickly correct you—the only thing that makes life worth living is actually discussing sex with friends over wine beneath starlight, but I do agree that crushes are huge for vitality, motivation, muse-discovery, etc. Unfortunately, it sounds like your crush is doing more harm than fun. Before we get to the “my boss” of it all, pining for a happily married man is fruitless and ultimately boring. If he was unhappily married, I might condone, like, flirting with him for a few days for attention—and while I used to romanticize affairs in the abstract, I do not endorse them. In my youth (20 years young), I hooked up with a guy who had a girlfriend and then she sent me 79 Facebook messages. I wouldn’t wish that on anyone!

I can say from experience there is nothing fab about being involved with someone who is involved with someone else, regardless of what poison The Movies squeaked into our soft little brains. You deserve to obsess over and eventually love someone who is available to do the same towards you. But I think you know this, because the truth is this crush is not so much a crush as it is a placeholder for something that is missing in your own life. I know, how inconvenient! We all know that even if you got to be with your boss you’d be like…Okay what now vibes?

You are not controlled by this crush, you are controlled by the high that obsessing over this crush gives you! Love addiction, ever heard of it? My old therapist was addicted to telling me I was a love addict I was like…yeah…what’s bad about love? But I eventually found that when love gets in the way of your work and autonomy, it’s time to reassess.

I would normally tell you to stay as far away from this person as possible, but I recently heard that he is literally…your boss. Not ideal. Obviously, I need a lot more info like—what does a boss do? What do you do for work? I do believe 99% of jobs are emailing (exceptions include surgeons, plumbers and people who press go on the rides at six flags). This sounds drastic, but is it possible to start looking for another job? It sounds like your feelings for him are coloring your entire professional experience and that sounds far more messy than rewarding.

Whether or not you eventually find another gig, you’re working for him right now and you need to respect yourself and your professional ambitions by keeping things as brief and work-related as possible. Easier said than done obv lol. But the good news is, your love of passion and obsession as evidenced by the fervor of your workplace crush, can, with some practice, be applied to another object of desire—maybe even to…yourself! Imagine! Of course, self-love and actualization is the ultimate goal (call me if you figure out what that feels like), but in the meantime I promise there are so many wonderful/terrible unavailable people you don’t work with that you could obsess over instead! Log off and get in the mix, sweetie!

I had my first first taste of fame the other day after I listened to Seek Treatment, thought to myself, “I think I'm funny,” posted a video on TikTok, and got a few thousand likes and views. I'm not obsessed with fame (yet) but wondering, what should I do with this while the algorithm is still in my favor? Any other reflections on TikTok, viral videos, and having everyone fall in love with you without caring too much?

No matter how much external validation you get, it will never be enough to fill the void that is inside!!!!!!!!!!! Now write that on the blackboard in cursive 1,000 times.

We cannot (I’m including myself here because I struggle with similar questions every 13 seconds) make work to get likes. No great art comes from trying to please everyone or worse, an algorithm. The Algorithm (which will be name of my first born btw) is not in anyone’s favor, it is a senseless machine slurping up our faces and beaming them into space so that we buy more overpriced athleisure. By the way, I just got a chic athleisure skort that I can’t stop wearing! S.O.S.

I’m obviously honored that my narcissistic and depraved podcast inspired you to make something. Making things is divine. My new thing is trying to find god and god’s whole thing is creation. So when we make art we’re literally cosplaying as god and are therefore elevated above the earthly concerns of our peers that so often drag us down (i.e. fame). The impulse in you to create and share those creations is stunning and will save your life!!! Keep making things when it feels good. Stop when it doesn’t. Never do it for the likes.

I honestly think TikTok is so funny & taught me how to not cry when I cut onions, but it also terrifies me. I wouldn’t wish a viral video on anyone! Even though we are technically people, we are basically just animals with base desires and love nothing more than worshipping someone as they rise to fame only to tear them down and celebrate their demise. (#FreeBritney)

I’ve been on three dates with this guy (he is straight from the movie version of my life) and he suddenly cancelled on me because he “was” “ill.” Do you think that he just wants to be friends? We did kiss once but it could have been platonic. How do I inquire into this matter without the mortifying ordeal of asking?

Oxymoron is the kind of word that people love to use in 8th grade English class, but I always forget what it means. Okay I just looked it up and I was right in that “platonic kiss” is an oxymoron and that he wouldn’t kiss you after a date if he wanted to be just friends.

I also know that everyone who is ANYONE (i.e. moi) has some random disgusting cold right now thanks to emerging with abandon after a year of hiding in our little caves. He probably... is ill and doesn’t want to get you ill which is actually? BKPE (big kind person energy).

Give it a week or so, see how he’s feeling, and try to reschedule. If he continues to cancel or seems distant then maybe he’s not interested. Ever since time lost all meaning in March 2020, three dates is essentially a long term relationship, so I think if he doesn’t want to see you anymore, he owes you a convo—one that you might have to broach yourself. You got this. You’re the main character honey! (I learned that phrase from Gen Z, which is of course a state of mind.) Only protagonists write into sexy online advice columns. XOXO