Sex & Relationships

“We Had the Perfect Date and Then I Never Saw Him Again”

Our wicked-smart sex and relationships columnist, Kate Carraway, to the rescue


Tom Cruise and Penélope Cruz in Vanilla Sky enjoying, what FLARE‘s entertainment editor Briony Smith, calls one of the all-time cutest dates in film (Photo: Everett Collection)

Dear Kate,

I went on The Perfect Date with The Perfect Guy over a year ago. We shared cups of ice cream and walked all over the city and ended the night at his condo where we kissed and played games until sunrise. It. Was. Magical. He went on a work trip that ended up keeping him almost across the country for months, off-and-on, dashing my hopes for a relationship with him. When he came back I was already seeing someone, and at some point he started seeing someone. Lately the uptick of his Facebook activity and the change in what he posts about says to me that he might be single now. I would love to pick up where we left off, but I don’t want to run the risk of being wrong. We chat on Facebook occasionally; should I flirt more aggressively? Ask him out as friends and suss it out?

Congrats: circumstance has left you to scavenge your own dating past without all of the reasons that usually makes this a bad, brutal idea. But first: you can’t—now, or ever—“pick up where [you] left off” with a one-night-only guy. Even if months (years?) hadn’t already passed, there’s just no doing this. It’s hard enough to reactivate with your best friends when one of you moves away. Your ice-cream-chemistry happened long, long ago, and you’re remembering, amplifying and imbuing a single experience with the optimistic sunrise-yellow of your Perfect Date’s perfect ending, which has been preserved in its perfectness only because it ended right there, perfectly.

(Also: hmm. Do the best relationships come from the best dates? When I isolate the best-ever dates I’ve been on—and “been on” doesn’t really account for how my leveled-up adorability and positive attitude and refusal to pay for anything contributed so essentially to those dates—they were never with guys I ended up falling in love with. Do we care if the best-ever dates lead to the best-ever relationships? YMMV, I guess.)

So, mentally and emotionally scrapbook your night with The Perfect Guy, sure—very few first dates are even semi-OK, and you owe it to yourself and all of us to maintain an HD-memory of a great one—expecting it to reanimate in the same form will only let you down. Sorry, but, banking on something that you’ve hyped into something else, something imaginary, isn’t cool. You know what is cool? (A billion dollars.) What’s cool is that you can relieve yourself of the flattening pressure of a high-stakes do-over, and re-approach the excellent, exciting idea of there being a CUTE BOY who is possibly SINGLE and you already have evidence that you might ACTUALLY LIKE HIM. Picture me beside you doing a big “Weeeee-oooooh weeeee-oooooh” alarm-sound. This doesn’t happen that often. This is where it gets good.

So rarely, more rarely than an occasion of A Perfect Date, are we gifted with such a nicely constructed dating scenario. You already know this guy, and even though you have dutifully followed my advice and abandoned all of your loaded-up expectations, there is a thin, glittery, elastic-y thread between you to play with. You know that at least some historical version of him is into you, attracted to you, responsive to you. You don’t have mutual friends (if you did you would obvi know if he was single or not) and you’re not friends-friends with him now anyway (good), so who cares if you ask him out and he’s taken? “What’s up / r u single rn? / Cool me too let’s get steaks” or “Cool good luck etc.” is effective. More delayed-gratification-ishly hot, though, and more respectful of your own human need for a steady drum-beat of sex-excitement, even as it comes to you via social media, is laying down some flirt-energy and seeing how he responds, and in so doing making sure you aren’t reverse-engineering your interest in him.

Within all of the mystery-minus-whatever-you-snooped-on-Facebook, and all of that space and time from then to now, there is fun, potential, and opportunity, for something, but who knows what something. This is why dating—for all of its heart-crushing, soul-deadening realities and eventualities (seen Gone Girl yet, btw?)—is so enveloping, sometimes so… everything: once in a while the possibility itself is what is Perfect.

More great advice from Kate:
Help! My Boyfriend and I Are From Different Worlds
Help! My Friend Has Become a Selfie-Obsessed Monster
Help! My Girlfriend Is Always on a Diet
Help! My Boyfriend Is Better Looking Than Me
I’m So Tired of Hearing About My Friends’ Boring Babies.
I Have Proof My Friend’s BF Is Cheating. Do I Tell Her?
My Best Friend’s Life Is Perfect. Can I Tell Her to Stop Complaining Already? 
How Young Is Too Young?
Is Long Distance a Dealbreaker?
When Do I Need to Disclose My Dismal $$$ Sitch?
How Can I Curb My Tinder-Rejection Sads?
When Should My Guy & I Talk “Numbers”?
Can We Be FWB When He Wants More?
Is It Ever OK to Date a Friend’s Ex?
How Do I Get Over a Guy?
Why Aren’t I More Obsessed With My BF?
Should I Propose to My Guy?