You Asked: How To Get Dressed For A Date
You Asked: How To Get Dressed For A Date
Jessica Graves answered. Plus meet-cutes and attachment styles.
When Jessica Graves, the uber-stylish brand guru and fellow Substack author of The Love List, canceled on a date to have oysters by herself, she never expected to end up on another date with a total stranger. A stranger who would quickly become her person; it’s a story straight out of a movie — girl ditches the wrong boy to hang with herself and instead falls in love with the right boy in the rain. Now, years later, Jessica talks about her meet-cute, the power of saying yes to the unexpected, and attachment styles. Plus, tips (and links) on what to wear for a first, second, and third date!
"In my early 20s, I dated a professional rugby player, who in hindsight (like always), was all wrong for me. One weekend long after we'd broken up he invited me to watch him and his teammates play against the Atlanta team. What can I say? I was single, and he was a 6 '6" rugby player. Naturally, I accepted." Jessica said with a laugh, thinking back.
She recalls her “ah-ha!” moment. "Day of the match, I got all dolled up and headed to the game. On my way over, it started to pour. As I looked out the car window, I imagined how awful it was going to feel to sit in the rain getting drenched so I could wave at a boy I used to date from the sidelines. Then it hit me: What am I doing?!"
"Immediately, I asked the Uber driver to turn around and take me to this famous off-the-beaten-path spot in an old train station in Atlanta called the Kimble House. Owned by friends of mine and known for their incredible oyster program and James Beard-awarded cocktails, I planned to sit at the bar solo, order half a dozen Blue Points and two martinis, and get appropriately drunk before heading home. If the rugby player can chase an egg-shaped ball around the world, he can certainly chase me to dinner if so inclined."
“It sounds like you sent a message to the universe,” I said. "No more chasing. They can come to me."
"Totally," she answered with conviction. "I figured I'd rather be with myself than be some girl waiting sadly on the sidelines."
"Martini in hand, I hardly noticed that a guy sat down beside me until he leaned in to ask, ‘Are you dining alone? And, can we eat together?’ I looked at him apprehensively but then nodded ‘ok’ as he ordered me a drink.” Pausing to consider her next words, she continued, "A former me would have said no and dismissed him for a million made-up reasons. But uncharacteristically, I said YES!"
"He told me his story, and I told him mine. We ordered another round, ate oysters, talked some more, and stayed until closing. Afterward, we walked hand in hand in the darkened balmy night. Then he kissed me in the rain. It was nothing short of a fairytale and we've been together ever since," Jessica concluded as my heart fell out of my chest and onto the floor.
Fate, some might say. Or perhaps the lesson here is to follow your instinct.
At that moment in our interview, Jessica's dogs began barking in the distance as Kevin came home from the gym and greeted her with a kiss before disappearing into the background. The two have been inseparable since those first oysters. They’ve had many dates, moved from Atlanta to NYC together, found a place in Gramercy Park and settled into life and careers.
"Before that, I'd been single for nearly 10 years! I'd gone on what felt like a million dates and was completely disheartened by the process. I'd sworn off apps and was ready to give up on dating entirely," she declared.
Jessica went on to describe how, at the time, she was tired of going on dead-end dates and falling into textbook runner/chaser dynamics with men like her dad. She was ready to meet her person. In January of that year, a few months before meeting Kevin, she ended her last and final situationship, and everything changed. And while the guy is irrelevant to the story, the work that relationship led her to is not. It caused her to do two things: one, read the book Attached, and two, get really clear about what she wanted in a partner.
"First off, I can't recommend the book Attached enough – it's a game-changer. I finally understood and identified my attachment style and began to attract guys who matched mine," Jessica revealed.
That sounds very empowering, but begs the question: How does that translate into a real-world scenario?
"Kevin was different. He was available and made that clear which put me at ease and allowed me to show up as my best self," she remarked wistfully. "The littlest things made all the difference and never activated that anxious attachment part of me. For example, he would ask me out on the next date while we were on a date, removing any and all anxiety about whether or not I would see him or if he would call. In short, his attachment style worked with mine."
Compared to the Peter Pans that came before, Kevin was everything they were not. “He’s an old soul.” Jessica regaled. “He’s in bed by 8:30 pm. He wears his seat belt. He’s calm. He always calls when he says he will.”
"Prior to him and reading Attached, I was stuck in the same old patterns that I’ve seen a lot of girlfriends in too – all of them are pretty, accomplished, and cool but have had trouble dating. But every single person I've told to read Attached has met their person within a year."
"Secondly — and bear with me because this sounds a little ‘manifest-y’ — I took pen to paper and wrote out what I truly wanted in a partner. Detailing things like how he makes me feel in the present tense as though I was grateful I already had it. There's something to this practice that allows you to be super honest with yourself because it's just you and the pen. After I finished, I stashed the paper away and forgot about it. A year after dating Kevin, I re-read the letter and it described him to a T. Moreover, if you had asked me years ago who'd I'd end up with, I would have given an entirely different description."
“I'm not surprised; there's what we think we want, and then there's what we actually need, and the universe teaches us that our preconceived ideas and notions are often wrong,” I remarked.
"You're so right. At the end of the day, you must be ready for the possibility of the unknown. And while fate may present you with the opportunity, what you do with it is up to you,” Jessica concluded with absolute certainty.
And, in case you find yourself on a date with fate, Jessica shares below what to wear for a first, second, or third date and beyond!
For a first date: If I can give you any advice, reach for a no-fuss outfit that feels elevated without being high-maintenance.
For a second date: White and vintage-looking leather is always yes. Again, go for a pulled together yet effortless look.
For a third date: Now here’s where you can be a little more playful. Bare legs (even if it’s winter) or tights and an oversized sweater.
To meet the parents: Think chic and classic, not trendy. Wear pieces that your hope-to-be mom-in-law can’t help but complement.
