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Run Away with Me? A First Date with Carly Rae Jepsen

What's it like to go on a date with an artist who's made a career out of capturing the feeling of having a crush? Like nothing you would imagine.

by Kyle Kramer
Nov 25 2015, 7:20pm


Carly Rae Jepsen, left, with the author / Photos by Seher

What kind of flowers would you buy Carly Rae Jepsen? How, were you to find yourself standing in front of a wall of plants that each in some way communicated a slightly different shade of affection, would you choose your offering to someone you had never technically met but with whom you felt you felt a certain ideological kinship and who, moreover, was essentially the standing pop cultural authority on said affections? How would you say “I'll make time for you, potentially” or “there's an outside possibility that I might really really really really really like you” or “we're about to just meet, and this is absolutely crazy, but I'll probably offer you my number for you to call, maybe” with just one bouquet? Whatever the correct answer is, I certainly didn't have it on the recent afternoon on which I found myself headed to meet Carly Rae Jepsen for our very first date.

I did know, however, that nailing that flower handoff moment would be worth it. Carly Rae Jepsen is perhaps contemporary music's premier romantic, an expert chronicler of the subtle push and pull of love in all its stages, particularly the ones yet to come. Her songs capture the rush of excitement that comes with those first flutters of tentative infatuation, the thrill of becoming accomplices in the adventure of life with another person, the searing disappointment of affairs discontinued, the warm nostalgia of passions unrealized. Hearing the saxophone that kicks off her most recent album, it's impossible not to feel as though all possible futures are opening up in front of you, as though you might at any moment bump into the love of your life in some impossibly cute encounter. Every grocery store aisle, every subway car, every moonlit evening becomes laden with potential. To impress Carly Rae Jepsen on a date would be an immeasurable coup. After all, listening to her music is like being in a constant state of having a crush on someone—just listen to the way she breathes the words “I wou-ld throw in the towel for you boy” on the final bridge of “Warm Blood,” as I have done probably a hundred times, and see if you don't get butterflies in your stomach. It doesn't hurt, of course, that a fair share of her songs are literally about crushes, but her voice sparkles such that even the kiss offs seem to emphasize the kiss, to show such a firm dedication to the romance of romance that they prompt grandiose fantasies and idealized visions.

Needless to say, I had high hopes for our date.

That's not to say I went into things with unrealistic expectations. I happen to have the kind of overactive imagination that thrives on the premise of Carly Rae Jepsen's music, that is quick to imagine the possible courses my life could take as soon as I meet someone. By the end of the first date, if I haven't envisioned the hypothetical unhappy speedboat crash that will be our mutual undoing (ugh, don’t get me started on the boat payment! I don’t even like boats!), gone on to rule out marriage and, by extension, put aside the possibility of a second date, I've instead at least pictured a couple cities we could live in. But I can recognize a contrived premise when I see one, and there was no getting around the fact that this date had been organized through her publicist, over the decidedly unromantic form of work email. There were none of the delusions that might come with a date that had sprung up out of an adorable chance encounter or even the kind that might arise from a chivalrous slide into my a prospective paramour's DMs. All I was expecting was that maybe, through the relaxed atmosphere of our encounter, we'd kick off a lifelong bond that would compel Carly to always put me on the list for her future shows and that we might, in the course of our hour together, land on a few definitive answers to the age-old questions about love and relationships that have stymied human beings for millennia. I just needed the right bouquet of flowers to communicate “hey, let's unearth a few timeless philosophical truths together and maybe add each other on Snapchat later.” Just like any date, I suppose.

I had the rest of the details ironed out: We were meeting at East Village ramen hotspot Ippudo, the kind of place I might, under different circumstances, take a date to impress her and instead humiliate myself by not being able to get a table. However, I'd already made a call in which I'd repeatedly dropped the words “celebrity,” “secluded corner,” and “strikingly handsome journalist companion,” and I arrived uncharacteristically early to sort everything out with the manager, George. He filled me in on the restaurant's history and showed me the aforementioned secluded corner (the particulars of the strikingly handsome journalist companion being self-evident). I felt like a regular Hitch, from the movie Hitch.

Minutes later, there was Carly, along with her publicist Lisa, the Cyrano of our date. Carly was smaller than I'd imagined, wearing an oversized pinstripe blazer and silver patent leather shoes, and even nicer than I’d expected—not so much the famous person who imperiously commands the room as the type who puts people at ease. As we made our way back to our section, I joked about how I always tried to reserve as much of the restaurant as possible for my dates, and, not only did she laugh, but she also touched my arm. Nice. We were charming each other already.

That's when I pulled out the flowers, and things began to go downhill. I spent a few moments awkwardly tearing away the paper around them so they would be more photogenic, and then I handed them over. What kind of flower had I bought Carly Rae Jepsen? Carnations. Yellow ones.

“Yellow is the happiest color,” Carly, who is incapable of being unkind and also somewhat of a pigmentation authority, via having a song called “Favourite Colour,” told me. “When I was little my parents told me that I could paint my room any color I wanted, and I went for sunshine yellow.” Great job, me! “And I regretted it every day after because I never really had nighttime in there.” Oh.

At least here we were, bonding over our childhoods and interior decorating. We made some small talk about flea markets (she’s a fan and decorates like an 80-year-old; I had nothing to contribute because I exhausted my annual furniture budget on a single shelving unit from IKEA) and ramen, and then we dove into the types of subjects anyone who lives in New York inevitably discusses at some point: New York and careers. In Carly’s case, the New York phase of her career came about because, in the wake of her 2012 album Kiss, she landed the role of Cinderella on Broadway, which obviously outstrips every one of my career accomplishments in New York by a fair margin. In mine, well, we didn't discuss that. It occurred to me that a not inconsiderable portion of the thrilling storybook outlook of Carly’s music might genuinely be tied to her actual outlook on life, that Carly might be the kind of person who, beyond her obvious talent, has the kind of charmed, Secret-like optimism that manifests its own reality.

“It was like that perfect bohemian New York life that you dream about,” she told me of the parties full of musicians she would throw in her Soho apartment, once again almost instinctively conjuring up exciting scenarios for the imagination. She excitedly told me about recently going on a safari in South Africa and about her thrilling days as a young musician in Vancouver after she’d decided to drop out of performing arts school to write songs. She rosily painted her days of throwing shows at the coffee shop where she worked and eventually forming more or less the same band she tours with today, musing about the joys of spending time on the road with them, “How could life be better than to be here with your buds?”

She told me how her hometown of Mission, British Columbia, had given her her own official day after the third-place finish on Canadian Idol that took her career to the next level.

“Does it change if there's a new mayor?” she asked me, the person in this situation with far less relevant life experience to draw upon. “If the old mayor gave you a day does it go away after you get a new mayor?” I responded by going off on a tangent about Houston rap.

If you'd asked me halfway through, though, I would have reported that we were really hitting it off. It was a great lunch! Certainly better than the lunch I would have been having with the socially inept losers back at the office, who, unlike me, were not exchanging bouquets of flowers with international pop icons. There wasn’t a spark, per se, and I was clearly outmatched on every front, but we were chatting it up! Naturally, we got to talking about our obvious shared interest, music, which gave her an opening to talk about remembering her early memories of listening to Rufus Wainwright on the train and being inspired to move to Vancouver. That in turn gave me an opening to utterly embarrass myself by describing the era of my life when I would ride the train and listen to her song “Tiny Little Bows.” But as we started to talk about songwriting—Carly loves the collaborative process, loves working with Sia, etc.—I realized we were drifting into a cliché interview, which, Carly inadvertently reminded me as we talked about balancing work obligations like interviews with her personal life, is a large part of her job.

Eager to steer the conversation away from that, I brought up relationships. What does her family think about her songs? They’re all incredibly open with each other, although her brother does tease her about the lyrics of “Didn’t Just Come Here to Dance.” Fair. How does being a famous musician affect her romantic life? “I wouldn’t want somebody to make a big deal or be turned off by it—or being turned on by it would be weird too.” OK, extremely good thing I wasn’t being weird right now. How does it work dating and traveling all the time? You have to find someone who’s down to tag along or great at communicating long distance. For instance, “Right now I have a boyfriend who’s great at both. If we have to go long distances, there’s no drama and it feels pretty chill, and if we have chances with his work and my work where it’s like ‘hey, you wanna come on safari’ he’ll come do it… We don’t get to see each other all the time, but we get to see each other in awesome places.” Damn, curved for ideal safari boyfriend. It’s like that sometimes.

“Am I preaching for no good reason about relationships? I do that a lot,” Carly concluded. But no, this was what I was here for, to absorb this information straight from the source, to stumble upon those irrevocable philosophical truths, right?

“If this was my first real date date, I would ask you five questions,” Carly added, once again practically curving me out of the restaurant but also saving everything. “Want to hear them?” They were great, of course: Would you rather have five kids or none? Would you rather be the richest man in the world or not? Would you rather die a heroic death—“like save a baby that was in a shark tank on a plane”—at 55 or a quiet one at 120? Would you rather be divorced twice and find your absolute soul mate at 60 or marry young and never be quite certain it was the best person for you but always be generally happy? Suddenly, entirely thanks to her, our date was going great. We saw eye-to-eye on everything, and we were yukking up a storm while landing on some of the promised revelations.

“I like that we’re acting like this is actually going to happen,” she laughed, in her warm, shimmering laugh. Carly really did have a way of understanding romance, but we also understood each other. Of course five kids would be better (“says the man, who doesn’t actually have to go through it five times”). Richest man? Too much responsibility. Heroic death? Overrated: “I know! So many people pick the hero thing! Who cares! You’re dead!” Marriages? A toss-up, probably.

We got cut off as we were making our judgement on that one, and as we posed for a couple pictures together to remember this special day by, we discussed the final question: Would you rather deal with the same familiar issues and challenges your whole life or handle those ones and then be given a mystery box of new ones to tackle? I chose the latter, explaining that’s what life is like anyway. I mean, inevitably we’re all going to have to deal with cancer or something at some point, right? Carly gave me a disapproving look and told me it was a grim way of looking at the world. Once again, I admired her optimism. Yet again, I don’t think she admired me. I say this also because at this point we returned to discussing the flowers, and it came to light that the price tag hadn’t been removed.

“$4.99? These were only $4.99?!” I stammered about my writer's salary (confirmed surefire date success move), about the selection at bodegas this time of year (confirmed weirdo move), about how this was all pretty hilarious when you thought about it. Things were getting awkward. But she laughed. Nice. This was it. I gave her my number on a napkin, first scrawling “Call me maybe?” and joking she probably got that a lot. Not so much, she reassured me. Now it was more “I really like you.” Not even my reference to how cliché my reference was was cool. But we laughed some more.

Carly really was incredibly nice, and we had hit it off, if not in a date sort of way or even lifelong bond sort of way at least in a "this was fun and an enjoyable use of our time, so let’s follow each other on Twitter and do it again some time sort of way." Yet while Carly does follow 90,000 people on Twitter, it didn’t end like that. Instead, she and Lisa realized the time, said their kind, effusive goodbyes, and swept out of the restaurant.

Then I looked down. On the table beside me were both my flowers and the napkin on which I’d written my phone number. It turned out that this whole flight of the imagination was just that. Carly Rae Jepsen could summon fantasies out of thin air, but she was happy to leave them floating there, too, not fully claimed. I trudged back to work with the evidence of my defeat in hand, the wisps of what could have been floating off into the brisk afternoon air.

“She brought you flowers?” my coworkers asked, impressed until I explained what had happened. When they had finished falling out of their chairs laughing at me and mercilessly owning me in successive waves with innumerable barbs about my incurable lameness, they explained what a terrible choice I’d made. “Carnations are like flowers you get your grandma,” one said. “In the UK, yellow is what you get people when their relatives die,” another added, apparently oblivious to the fact that Carly Rae Jepsen confirmed it’s the happiest color. “Really, you didn’t remove the price tag?” the Greek chorus of shamers chimed in.

That night, my ego still bruised from the jabs of my coworkers, I went to Carly's concert, where, despite my elaborate fantasies, I had not been invited backstage to schmooze with cool celebrities. Instead, I found myself as the third wheel to two separate pairings of friends, confronting infatuation and human interaction in all its stages. People danced and made out around me, and I sang along, happy, for the moment, to be back in this idealized pop world. Onstage, she shouted out her boyfriend, who was in attendance, launching another barrage of jokes in my direction. But just as Carly had told me she loved having all her songs as little vignettes of moments in her life that were sometimes just the tiniest sparks writ large as fantasies, I had each of these songs as a reminder of our brief foray into what could have been. The concert, of course, was flawless. That saxophone! Anything could happen.

As we filed out, Haddaway's “What Is Love” played over the loudspeakers, prompting me to wonder once more, the only question that song prompts anyone to wonder: What is love? What is the strange alchemy that makes someone more than just a person you've shared an entertaining meal with? What is it that makes the possibilities of future encounters with another person spring so vividly to life, that compels you to stay just a little bit longer at the party to talk to your crush, that pushes you to make decisions well outside of your self interest because of some doomed obsession with a partner? I think a lot of it is there, in those songs, although Carly and I never had the revelations at lunch I’d imagined. She never even added me on Snapchat. But things never work out quite the way you picture. That’s why we escape into the fantasies in the first place. So what is love? It's something that, despite all your best intentions, you don't pick the right bouquet for, until you do.

Kyle Kramer is not the type of guy to call more than a friend. Follow him on Twitter.