My Girlfriend Is Way More Successful Than I Am — & 16 Years Older

Laura Brown walks in to Per Se holding the hand of a young man with above average hair in dark jeans and white Ralph Lauren button-down. The hostess smiles at the pair. "Good evening, Ms. Brown. Sir, would you like to borrow a jacket?" Befuddled, he replies, “No thank you. I’m actually a bit warm.” Laura pinches his arm. “There’s a dress-code, you goose.” The hostess disappears and returns moments later with a Per Se labeled sport jacket that fits the young man more perfectly than any garment he has ever worn. Embarrassed by his faux pas but feeling très 007, he struts half-inflated into the restaurant. Per Se has a 3-star Michelin rating; dining there is like finding out Santa Claus is real and put you on the Nice List. Laura received an invitation as congratulations for her newly appointed position as editor-in-chief of InStyle. I am Brandon, the young man clinging to her arm in a borrowed jacket. We follow the hostess to our table, which is adorned with a festively handwritten placard reading: "Laura Brown (And Brandon!)." The whole evening seemed to perfectly caricature our relationship, which began a bit over a year ago. I was living in Los Angeles using my B.A. in English as a shower curtain, performing stand-up comedy, and working as a waiter at the Sunset Tower Hotel where Laura frequently stayed as a VIP guest. One notably flirtatious morning my computer fatefully malfunctioned. I handwrote her bill and included at the bottom a cheeky prompt for her phone number (first and only time I pulled this, hand on heart — for you statisticians out there, that's a 1.000 batting average).

I flew to New York City to meet her for our first date, and have since swapped coasts to live with Laura in her lovely Manhattan apartment and to continue my meteoric rise to global stardom (or being a stay-at-home dad — whichever comes first). Laura is 42 years old. According to the “half your age plus seven” algorithm for social acceptability of age difference in romantic relationships, my 26 years on this planet puts us just on the spicy side of decent. But here’s what I think: Once you’re in the pool, you just want someone to help you swim. I do occasionally spend time with people in my own demographic (what can I say, I'm versatile). And when I do, a pattern repeats itself. The conversation goes through the usual motions of, “How are you, where do you live, how’s your Instagram follower ratio coming along…” until someone eventually asks, “So, how’s your girlfriend?” Others chime in, “Yeah, what’s that like?” I think the curiosity stems from a combination of genuine interest in the age gap between Laura and me and the fact that she is successful — and quite publicly so. It seems only appropriate to answer these questions somewhere they’re less likely to read: a women’s lifestyle site. So, what’s it really like to date an older woman who is crushing her highly visible career in the fashion world, and most importantly, is a legend on Instagram? What first attracted me to Laura was that she sat in my section. But I found myself lingering near her table, drawn to her open, unaffected, fun-loving nature. She laughed at my jokes. She has a clear and bright enthusiasm that bleeds into her every interaction, as if she’s saying, ‘Well here we both are, whaddya got?’ And whoever is in front of her — waiter, actress, TSA agent — inevitably lights up. I mean, every damn time! It’s bonkers. Anyway, we had established enough of a banter that asking for her number seemed a natural progression. But once I saw she had actually written it down, I became terrified, realising I had crossed a line I had tacitly pledged my employer I would not cross. She sensed my fear and egged me on. Her exact words were, “Text me. I dare you.” I later sent a text that I believe ought to be archived in the Smithsonian. It read: “Hello. I have a long history of backing down from dares, so please know that texting you is taking a whole lot of pluck.”

At the time, I knew nothing about the fashion world, had never bothered to even try to dress well, and had no clue who Laura Brown was. As our text messages zoomed back and forth across the country, we began to call each other, as Mr. Graham Bell intended, and our budding romance spilled over into Instagram interactions that some of my friends noticed. I became more aware of the prominence of Laura’s position in the fashion industry, and I’ve seen how hard she works to earn it. I think the things I love most about her are the very same gifts that have driven her success: Her sunny disposition, quick wit, and obvious comfort in her own skin allow her to shine anywhere. And she is thoroughly decent, irritatingly creative, and has razor-sharp instincts, encouraging whomever is in her audience to feel naturally themselves. Put it all together and she can come up with an idea for a cover shoot, convince the celebrity to do it, ensure the shoot is a positive experience for everyone, write the story to go along with the pictures, and share charmingly captioned behind-the-scenes looks to get the general public interested. And make real friendships along the way. I feel like I’m laying it on a bit thick, but it really is impressive to behold. But so is seeing her fizzle out at the end of the day, and that’s why God invented pasta, wine, and Netflix! But…nobody cares. They just want to know, “What’s that like?” You know, dating an older woman.

Well, it’s a lot of things. One, Laura is kind of a big deal. So there are times when I am pulled up on the metaphorical stage. That’s intimidating. There have been instances when I’ve been tossed in socially with people whom I’ve admired, watched, enjoyed — people to whom I’ve been tuned in for years, who have influenced my life in some way. Laura’s job IS to be tuned in, and to comment, explore, interact, and share what she finds with the rest of the world. I run into problems when she leaves for the bathroom, and those of us left behind realise that she was the one running the show. I just hope that someone else picks up the reigns before the silence drags too long, as anything I can think of to say is inevitably horribly awkward. I recently found myself hyperventilating at an SNL afterparty, agonising over a botched interaction with a famous actress when, in fact, all I’d said was “Hello.” My big success that night was a latent compliment from Laura’s pal Kristen Wiig on my Donald Trump impression. I cling to this. There are plenty of moments that could be prizes on a game show. Win a chance to be styled by Laura Brown! Win a hike with Emilia Clarke! Win a trip to the Paris fashion shows! Win a dream vacation to the Bahamas! Listen folks, I’ve won so much, I’m getting tired of winning. (Not really — we just came back from Australia, where we drowned in adorable marsupials.) Also: She has a nice apartment. The ceilings are high. And it is full of interesting trinkets and books and paintings and photographs, all tastefully arranged. Her closets are full of nice clothes. It’s nice to live in a nice place. She smells good. She is pretty. But often, it’s hard. Laura runs a giant international publishing brand, and I ask strangers what they want to eat for lunch. One of these jobs pays more than the other, even with the gender wage gap. She pays for dinner 95% of the time (sometimes I spring for pancakes at the diner). I can’t even afford her dry cleaning. I have negative money. I owe $30,000 in student loans. I’m working hard, but am still in the early stages of my quest to build a career out of stand-up comedy and writing. And when I consort with Laura and her friends, so many of whom are successful, established — often, wildly so — I worry about the trap of thinking I have made it. I haven’t. In fact, my reward-to-work ratio is completely out of whack and I’m wary of losing the sense of urgency necessary to induce growth. Every time we go out to a nice dinner or stay in a beautiful hotel, I try to remember: I haven’t earned this life yet. I am reminded of this when I call down to concierge and am greeted with a “Bonjour, Mr. Brown.” It feels a bit like I am up on a narrow bridge and I don’t want to fall off into the flaming death volcano of entitlement. But on the other side of the coin, the world has just been struck by a giant orange asteroid with a combover. So, YOLO!

So, I do what I can to contribute: If I get home first, I arrange the apartment in a nice way. Pick up some wine. Light a candle. Artfully drape a Louis Vuitton throw. Take out the trash. I’ve also found a handwritten, illustrated note, left at random times, is not only a lost art, but a real winner with the ladies. Notes were a theme in our courtship and are something of an anchor in our relationship. Our apartment is literally littered with my tiny masterpieces. Some guys wonder if the relationship is emasculating. (After all, the male apes are supposed to go hunt the mammoth to provide meat and wool for the village women). But it’s 2017; Laura orders Seamless and gets a lot of free sweaters. I think it takes a certain level of confidence to be okay with our economy of scale. And in some ways, frankly, I made this woman. I mean, when she met me, she only had 70,000 Instagram followers. Now she has 111,000. Don’t try and tell me that’s a coincidence. When she met me, she was executive editor of Harper’s Bazaar — now she is the editor-in-chief of InStyle. I’m helping her connect with millennials — and Snapchat filters. Also, of course, I am using her, for money, connections, power, fame, clothes, career advice, motivation, sex, company, security, housing, food, and entertainment. But between the two of us we can’t rent a car. I don’t have a credit card, and she has no driver’s license. So, there you go...that’s what it’s like. I guess life has a way of evening things out.