The comedian and actress Catherine Cohen has made a name for herself as a sharp, irreverent chronicler of the often bizarre experience of being a 20-something woman. As the host of Cabernet Cabaret, a weekly stand-up show at New York City’s Club Cumming, she performs brassy, original tunes about rejection (“boys never wanted to kiss me, so now I do comedy”), UTIs, and running away from her problems by going apple picking with “13 of [her] closest friends and six of their sexual partners.” With her fellow comedian Pat Regan, she hosts the cult hit podcast Seek Treatment, on which the pair discuss “boys, sex, fucking, dating, and love” with their guests. Here, she tackles reader questions in the same vein. She’s not an expert. But she does know what she’s talking about. 

Have a question for Catherine? Email advice@wmagazine.com.

I’m a recent college grad and just moved to New York for a Devil Wears Prada–vibes internship. I love being a career woman (read: 22-year-old gay with a paid internship), but I want to be rich and married. How do I find a rich man to marry?—Sugar Baby

Hey my li'l candy gal,

First of all, congrats on the sexy internship—my first year in NYC I answered phones for free in a room where the floor was always wet. So you’re killing it. And now you’re telling me you want to be rich and married? Random! Sadly, I don’t know how to find a rich man—all the guys I’ve dated reply to my nudes with links to the GoFundMe for their web series about what it’s like to be young, but also confused. Hear that? That’s the sound of the ground breaking.

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I always assumed that if I walked into a hotel lobby, a rich foreign businessman with everything to lose would insist on buying me a gin martini and whisk me off to that bridge in Paris everyone puts locks on to symbolize their love. I wonder why that bridge makes me so sad. God, I’m interesting. So maybe walk into a hotel?

But first ask yourself why you want to be rich and married. Obviously, money makes life better and more fun (cut to me dropping $42 on “face crystals”), but it feels even better when you’ve earned it yourself. I feel at my most sensual when I’m using the Chase Bank app to deposit a dripping wet three-figure check. This isn’t sponsored by Chase Bank, though I do find Chase to be the sexiest bank. TD…sounds like an old timey disease you got while concocting a rare perfume near a dying calf in an underground vault. And Bank of America, it’s like…okay, you’re a Republican.

Anyway, get rich on your own. How gauche to have to ask permission to spend! And as far as the married bit goes? Well…it’s so vintage. I guess I celebrate people who want to get married, even though when someone tells me they are married, I black out and forget their name. But what do I know? I’m typing this on a laptop with a piece of pad Thai from 2016 stuck in the space bar.

How do I stop being a complete psycho and stalking the girls my boyfriend has previously dated on every social media platform? I am what you might call ‘j'addicted’ to comparing my hotness to their hotness, and I know this behavior is not healthy!!!! —Crazy in Love or Just Crazy 

Hahahahaha, I think about the girls my boyfriend kissed before he knew I existed more than I think about my friends and family. This is something I am…working through! Here’s what helps me: First, stop looking at their profiles. Does it ever make you feel good? Don’t you want to feel good? It is so much better than feeling bad. Wow, someone just knocked on my door and handed me a Pulitzer Prize after I typed that. When you feel the urge to look at their profile, imagine how you will feel if you look at it, put your phone down, and say “I am falling in love with the present” over and over again until your roommate is like, “Can you stop?”

Next, I get how hard it is to not compare yourself to these other girls, but can’t you accept that you and these other girls are both hot in your own way? Can’t two things be true at once? For example, I want Adam Driver to ruin my life fiscally and socially, but I also want Sufjan Stevens to murder me in a quiet bookstore. I don’t discriminate!

Lastly, I find it helpful to consider how I feel about my exes with regard to my current partner. Yes, some of my exes were (and probably still are!) superhot (okay, brag) and some of them were great in bed (double bragg) and even great people (triple braggg), but I don’t want to be with any of them at all! And how I feel about them has no reflection on how I feel about my number one cutie right now. Plus, isn’t it sexy that your dude pulls hot-ass chicks? He’s hot, you’re hot, get over it. Love u.

A guy I know recently asked me out on a date. I had a feeling he had a crush on me but I didn't really feel the same way, so I just let it be a vaguely flirty friendship until now. Is it wrong to go on a date with a friend if you're pretty sure you'd only be interested in a casual friends-with-benefits situation? If the date doesn't go well, is it possible to still be friends? Can you tell I haven't been on a date in years? —Single in Seattle 

Dear Single in Seattle,

Hey, it’s me!! Okay, so what I’m hearing is…a friend of yours…that you would have sex with…wants to go on a date with you…

Maybe I’m out of touch (I do still have an iPhone 7), but this sounds like good news!! Honey, darling, angel, baby: Stop overthinking and give this guy a chance. How do you know what it will turn into? How do people know anything for sure? Last weekend a guy at a bar (drumroll, please) told me astrology wasn’t real, and I was like, "One, stop flirting with me, and two, isn’t it more fun to believe it’s real?" Keeping an open mind is erotic, being closed off to new ideas is Not It. Okay…slant rhyming erotic with “not it?” I’m an artist. 

Anyway, go out with this guy, see if he asks you questions, see if he makes you want to put your mouth on (or even kind of in) his mouth, and try not to define it right away. If it doesn’t go well, I’m sure you can still be friends, but what does that even mean? Don’t we all kind of want to fuck all our friends? *I Jim Halpert stare into camera* 

On an unrelated note, you can change my mind about anything if you just talk kind of passionately about it for 45 seconds.

I like doing outdoor things, don't own many skirts or a blowdryer and never second-guessed my femininity until I came to Ireland to study abroad and every lady-student here looks and seems like they're cool and collected—sex kittens, even! (I.e., they have little purses, "adult" looking coats, lip wear other than Burt's Bees chapstick). For some reason, I feel like a little boy in a Paddington Bear coat in a sea of Grace Kellys, and suddenly am sad that feeling comfortable in being alluring and sexy has never been my strong suit. How can I get in touch with that part of myself, without having to change the way I look? —Paddington

Dearest Paddington,

I’ve never seen the Paddington film (is the film based on the bear or was the bear based on the film? We got a real chicken-egg sitch on our hands!) Either way, it sounds like you know who you are and what you like—what’s sexier than that? You’re probably just adjusting to a new environment and feeling a bit off your axis. Try leaning even more into who you are: Go for a long hike through the moors (is that Irish? I’m addicted to moors and their secrets), try a new fancy soap from a shoppe (very different from a shop), masturbate more! Science literally says it's good. 

Also, while I love the image of Irish sex kittens floating through space keeping their feelings all cool and wrapped up in tiny purses, just know that literally no one is cool and collected. One time, I was having a full-blown panic attack on an afternoon train to Paris because I remembered everyone I have loved and will love will eventually die, and a woman came up to me to say she liked my necklace, and that I looked very elegant. I was like, Still waters run deep, honey! So, don’t worry if someone else seems cool and collected. Besides—what’s sexy about that? My type is Nick Cage in Moonstruck meets Tony Soprano (SOS).