My Boyfriend & I Recreated Our First Date For Our Anniversary

Hannah Orenstein

After two years together, my boyfriend and I have had plenty of memorable dates. But one of my very favorite outings with Saul was our first, when we got drinks at a cocktail bar, then picked up slices of pizza. It was a pretty standard itinerary, as far as first dates go, but it feels extra special to me because that marked the start of our relationship. Even though I work just a few blocks from the bar, we surprisingly haven't been back together since that first night — until we recreated our first date for an anniversary celebration that turned out to be so much fun.

For maximum nostalgia, I purposefully wore the same outfit I had on the night we met, which was a black sweater, black tweed mini skirt, and black ankle boots. The process of getting dressed made me reflect on how much has changed in the past two years (the highlights: Saul and I fell in love and now we live together) and how much has stayed the same (I still own all these clothes and apparently take selfies in the exact same way).

He met me at my office and then we walked to the cocktail bar, a cozy spot in Manhattan's Gramercy neighborhood called Ampersand. On the walk there, I pointed out the street corner I stood on two years earlier when I pulled up his Hinge profile to "review" it before the date. (There's nothing more awkward than saying something on a first date like, "So, what's your dog's name?" and discovering that your other Hinge match is the one with the dog.)

Hannah Orenstein

Inside, we hoped to sit at the same table, but it was nabbed by another couple who sat down right before us. I ordered the same drink — a delicious bourbon, pear brandy, and apple cider concoction — and we agreed that this time around, we could skip our order of guacamole, since it wasn't that great. The bar appeared to be full of other couples, and it was entertaining to puzzle out which ones looked like first dates.

"So, how many dead husbands did you say you had?" Saul asked. I burst out laughing. On our first date, he had commented on the cocktail ring I was wearing, which was vintage and featured five big, costume jewelry "diamonds," and so the conversation had naturally turned into a massive joke about how I had faked the deaths of several ex-husbands and kept all my old engagement rings. (I realize this is the kind of dumb inside joke that only makes sense when you're caught up on date where the chemistry is crackling, the drinks are flowing, and everything seems hilariously charming. Bear with me.) Keeping on theme, we riffed on classic first-date topics, like which neighborhoods we lived in, how many siblings we had, and what we did for work. It felt strangely funny to re-live the exact discussions we had the night we met.

But of course, this wasn't really our first date. It was hard to keep up the façade that we were strangers meeting for the first time. We said "I love you," made dirty jokes, and talked about actual emotions, anxieties, and fears, which are all things I would've been terrified to do if this were actually a first date.

Just like we did two years ago, we left Ampersand and walked nine blocks down Third Avenue to Joe's Pizza, where we each ordered a slice to go. Our plan was to eat them while walking down Fourteenth Street to the north west corner of Union Square, where we had our first kiss. I slipped up and tried to kiss him while we waited for the crosswalk light to change, but he dodged me and insisted we wait until we reached the right spot. It sounds silly, but the anticipation that built up over the next few minutes mimicked the same kind of giddy excitement I had felt in the build-up to our real first kiss.

Hannah Orenstein

Unlike our first date, when we each took the subway separately back to our respective apartments in different neighborhoods, this time around, we hailed a cab back to our shared home. Though I'll admit we're sometimes tempted to crawl right into bed and watch Netflix after a night out, the evening felt strangely energizing. We stayed up chatting on the couch for a long time. When we finally did call it a night, it was comforting to recognize how our relationship has evolved in the two years since we met. I love falling asleep next to him now, rather than sending a "good night" text from across the city.

Truthfully, I hadn't expected that recreating our first date would feel so special. Saul and I do a lot of dinner-and-drinks dates, and while there's nobody else I'd rather trade stories with over cocktails and cheese boards, I assumed that this particular date night would feel pretty par for the course. Instead, the experience sparked flirty conversation, prompted a fun walk down memory lane, and made us feel proud of how far we've come as a couple. I don't know if we'll reenact this same outing every year, but it's nice to know that we can recreate the magic of our first date whenever we like.