#2638 Sex With Friends

Christian Slater Winona Ryder Heathers

Anon asks: Hiya Isaac. I recently slept with one of my best friends. It would have been fine, but he went out with another girl a few days later (which had been planned for a while and I already knew about) and they are now pretty much together (except he doesn’t want a serious relationship). I don’t regret sleeping with him, and we both know there are no feelings involved so the friendship is still intact. Which leads to my question why did he sleep with me?

Hey, gidday mate. I’ve gotta be honest, something about your question doesn’t make 100% sense to me. Do you really have no feelings for this guy? I detect a bit of a bitter tone in your words. No?

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#2637 What’s In Store At Maison Kitsune LES

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Maison Kitsune has a new brick and mortar location in NYC, on the quietly cool stretch of Rivington (between Chrystie and the Bowery) in the Lower East Side. Fellow retailers on the block include Green Fingers (which shares its backyard garden with Kitsune), Freeman’s Sporting Club, and Morgenstern’s Finest Ice Cream, meaning it’s fast becoming the ideal hang spot for anybody looking for a moment’s break from the traffic, the humidity and the noise so prevalent in the city this time of year. Moti Ankari and I paid the store a visit last Friday, and couldn’t leave without trying on some clothes; I’ve been reading my old Ivy League style books nonstop recently, and my number one takeaway has been cuffed pants with white socks, canvas sneakers and a button-down… See below.

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#2636 Dating Burnout + More!

Kanye West Paul McCartney

Anon asks: Dear Isaac, I find myself in a peculiar place. After nearly a year and a half of marathon dating (Tinder, OkCupid, Coffee Meets Bagel — you name it, I tried it), I took stock of what I wanted VS needed and I can say with complete confidence that I do not know what I want or what I need. Beyond dating disasters, I’m not happy at my job and I think the stress of it all has taken its toll. Have you experienced Dating Burnout?

Hey, gidday mate. I don’t know that I’d call this situation Dating Burnout, it kinda just sounds like temporary life dissatisfaction. If you don’t know what you want or need from a romantic perspective, why not stop exerting so much energy in that direction, and redirect it to more worthy pursuits like getting a job you actually like and enjoying yourself with your friends. As far as I can tell, relationships are supposed to be the icing on the cake, they’re not supposed to be the entire cake. If you’re not happy in yourself you are never going to be happy in a relationship, so work on yourself first, and the rest can come later!

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#2635 Prepping For Fall

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Hey, gidday mates! I did something I never usually do yesterday, and spent the afternoon in the Financial District with my Italian mate Jacopo Moschin (he shot these photos, then we played a rowdy game of squash). It’s a whole other world down there — you’ve got these ancient dock buildings pushed up against modern skyscrapers, ye olde New York bistros alongside luxury condos, and insane views of the water every which way you look. The weird thing, though, is that on the weekends it’s completely dead; the streets are empty, the eateries are closed, and there’s this eery Gotham City vibe that takes over the whole neighbourhood.

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#2634 Don Draper Off-Duty

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Hey, gidday mates! Happy Friday! As a self-confessed style nerd, I’d be lying if I told you I don’t obsess about the small details in an outfit. Because I do. I really really do. So recently, my number one solution to every sartorial conundrum has been: Tuck it in. No matter what. Boring old jeans and a T-shirt becomes a cool 90s movie star moment. A short sleeve shirt and dress pants becomes a 1950s candy man. And one of my most common outfits of late, a simple pair of khakis with a white T-shirt and denim button-down, becomes Don Draper off-duty; the kind of outfit the ad man would wear mowing the lawns or playing ball with his kids on a hot Saturday. You feel me? The key is to keep the proportions classic — notice my pants are slim but not skinny; the T-shirt is fitted, not sloppy; and the denim shirt is worn open like a lightweight jacket. Too easy.

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