What to Wear for a Romantic Valentine’s Day Date

romantic valentine's day date

Maybe it was the remarkably cold, dreary January this year, or all the fabulous dates I was watching on the Bachelor, but for whatever reason I started looking forward to H and I’s Valentine’s Day date AT LEAST a month before Valentine’s Day. We geared up for it with a Valentine’s Day tea the weekend before at Cherry Hill Farmhouse in Falls Church, which was campy but fun (think ladies in hoop skirts saying “Well, back in the olden days” and lots of fudge). We planned our big, romantic Valentine’s Day date for February 14, a Thursday. To add to my excitement, H planned the whole night, so I had no idea what we would do.

I started preparing for the date at least two weeks before Valentine’s Day, since I had to tell all my coworkers I would be leaving ~early~ to get ready. (Those conversations were really just my coworkers and I discussing how ridiculous it was that no one else had anything planned for Valentine’s Day, given that they are all married.) I also had to plan my outfit—I caved and ordered a new dress, which I rationalized by telling myself I could wear it as a wedding-guest dress, and a short faux-fur coat with an oversized collar, which I rationalized by thinking about all the times I had gotten dressed up and thought “how amazing and old-Hollywood glamour would I look if I had a fur coat to drape dramatically around my shoulders.”

On Valentine’s Day, I headed home around three to shower, blow-dry my hair, and primp before H came to pick me up at six. I wore the new dress, a cute navy number from J Crew with spaghetti straps and a lace overlay that falls to mid-calf. I had planned to wear the silver strappy heels that I wore last Valentine’s Day, but the stilettos with the dress were total overkill, so I opted for my trusty neutral heels instead. I kept my jewelry simple with sparkly stud earrings, a tiny gold necklace, and a simple bracelet. The faux-fur coat was perfect—I had dithered about whether I should order it in off-white or pale pink, and the off-white was great for a classic look. I finished the look with my hot pink Kate Spade crossbody purse.

Dinner at the Ritz

H brought over beautiful pink flowers (he knows pink is my favorite) and we got in an Uber. I tried to keep track of where we were, but was thoroughly turned around by the time we got to our mystery destination, a tall office building. A guard scanned tickets that H produced from his pocket and escorted us to an elevator. We got out on the top floor of what turned out to be the CEB Observation Tower in Arlington! The top floor had gigantic windows for a 360-degree view of Washington D.C. and Arlington.

CEB Observation Tower view of DC

We climbed one more flight of stairs to a champagne lounge, where we got glasses of bubbly and headed out to the observation deck at the very top. I’ve seen D.C. at night before, but never from so high up. It was really beautiful and, although there were other couples there, it felt like it was just the two of us looking out over the city. We snuggled together on a loveseat (I was glad I had my big coat) and enjoyed the view. When we got cold, we went inside to see the view in other directions—everything was labeled and there were exhibits with historic pictures of the city.

What to wear for a romantic valentine's day date

We left at 7:30 for our dinner reservation at the Georgetown Ritz, which was just across the river from the observation tower. The lobby and restaurant at the Ritz were super cozy—all low lighting and comfortable leather chairs and natural wood. We had another glass of champagne and a late dinner—most people had eaten earlier so, again, I felt like it was just the two of us.

My Valentine’s Day date with H was so private and romantic, and it was amazing to see Washington D.C. at night from the top deck of the CEB Observation Tower. I love surprises, and the whole night went so smoothly—even our couple picture taken by a stranger on the observation deck turned out well! Our date was the perfect way to celebrate another year together.


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