The Three Best (& Worst) Dates I've Been On

Ruffled Navy Top (So soft and cozy! I’ve been wearing it non-stop. Other recent purchases include this cozy twist top, this ruffled hem sweater, this wrap sweater, and this navy ruffle top.) / J.Crew Coat (Also love this one, this one and this one.) / Madewell Tote (And love this more affordable version.) / Stuart Weitzman Boots (In navy here. Love this more affordable pair, too. That pair also available here, here, here and here.) / Rag & Bone Jeans (So worth it. I had to have them hemmed, but they’re the most amazing white jeans I’ve ever owned. They’re soft and stretchy yet don’t lose their shape!) / J.Crew Headband

A few things:

I can’t get enough of this navy ruffled navy top! I picked it up a couple of weeks ago while shopping downtown with Mitch and Emma–they’re the best–and I’ve been wearing it non-stop. It’s been so cold in Chicago that just the thought of a polyester or silk shirt makes me shiver, but this top is crazy soft and cozy, and almost feels like a sweater or sweatshirt. (It’s brushed on the inside, making it super warm.) And it’s totally acceptable to wear for a night out! Such a find. :)

Since the days are getting longer, Mitch and I are back to shooting after he gets home from work. Of course, this means lots of dark photos, as the sun has almost always set by the time we get around to snapping pics. But it’s definitely nice to feature some looks that I wear during the week instead of just those that I wear on the weekends. I actually wore this outfit to dinner last night with Shaheen, Jess and Blair at Publican Anker, or “Pelican Anchor,” as I like to call it. ;) We’ve been trying to make girls’ nights a monthly thing, and I can’t tell you how much I look forward to them. So grateful for my Chicago Ladies! Also, please note the hot pink coat. Still goin’ strong with my Valentine’s Day theme! Two whole outfits. Killin’ it, Kelly…

In keeping with that whole Valentine’s Day theme, I thought I’d take a moment to relive some of the best–and worst–dates I’ve been on. But let’s start with the worst so we end on a positive note. ;)

The worst:

When I was in high school, my parents guilted me into going on a date with a kid who’d just returned from reform school. Yes, you read that correctly. I can’t remember the details exactly, by my parents somehow became friendly with his, and all of a sudden, I was going to the movies with a kid who terrified me. The car ride to the theater was pretty bad; we discussed some thing that I confessed I wasn’t a fan of, which led to a 10-minute stretch of total silence. At the movie itself, he tried to put his arm around me, and I freaked out, excused myself, and spent a solid 15 minutes in the ladies’ room. But I think my favorite part of the night was the end, when he asked whether we could jump on my trampoline. Of course, I said yes. (HUGE fan of trampolines right here.) He ended up accidentally jumping on top of me, though, and I had the wind knocked out of me. A night to remember…

Race car driving has to rank up there, too. I was trying really, really hard to step outside of my comfort zone and meet new people, but I ended up nearly hyperventilating out of fear. Also, the inside of those helmets? Yuck.

This one was more of an experience, but in college, I had a rough patch during which I attracted a frightening number of psychopaths. The first was a kid I became friendly with during the first week of school. He seemed nice enough at first, but I soon got the creepster vibe. Sure enough, one day, he left a note on my door that read, “Kelly: Meet me at 5 o’clock IN MY ROOM, ALONE.” No way, man. Why’d you put “in my room, alone” in caps? And when I didn’t show, he tracked me down and we had an hour-long conversation about how I wasn’t putting enough effort into “us.” The second was a guy I met while standing in line at the dining hall. A few days later, he located my dorm room and delivered an insane amount of (stolen) loose cookies from the dining hall in a giant black garbage bag. (Along with a couple of stolen plants.) The third was a kid who’d drive past my parents’ home on the reg and text me what cars were in the driveway. “White car today. White car AND black car today. No cars today.”

:-/

The best:

I’ll tell the full story in the next couple of weeks, but my first date with Mitch was a long walk along the East River on the Upper East Side. It was raining, but we walked anyway, without umbrellas (because we all know how much Mitch hates umbrellas), and we talked about everything. I know this sounds a tad weird (and maybe you’ll get the creepster vibe from me), but in the middle of that walk, I swear I knew I would one day marry him. The night ended with our first kiss right outside of the 6 stop on 68th Street. I’d never been happier.

When Mitch and I first started dating, we decided that we’d always do a “Christmas Dinner” for ourselves. The holidays get jam packed so quickly, so we wanted to reserve a night for just the two of us, to take in the magic of it all. At our first Christmas Dinner (Blue Smoke), I ended up crying because I was so sad that we were parting ways to spend the holiday with our respective families in Illinois and Vermont. But at our second dinner, I managed to hold it together, and we had the time of our lives. We got all dressed up and went to Wolfgang’s in Tribeca–something we never would have done at that point in our very broke lives, but goodness. It was just one of those nights. It was unseasonably warm, the food was amazing, the ceilings were exquisite (I’m so into ceilings at restaurants, haha), and the waiter was hilarious. I’ll never forget it.

Another one was celebrating our first Fourth of July together in Ocean City. It was a “pinch me” experience, for sure. I was falling head over heels in love with the guy of my dreams in my favorite place in the world on my favorite day of the year. And two groups of people were setting off illegal fireworks in the sand, and the two police officers (on beach cruisers) couldn’t figure out that they needed to split up in order to catch them, and just kept racing from group to group each time fireworks went off. We laughed until our stomachs hurt, and stayed out until the last firework exploded in the sky.

Okay, actually, just one more. That amazing night at Blue Ribbon Bakery (a restaurant, not a bakery) in the West Village. We were celebrating two years of dating and simply stumbled upon the spot while looking for the perfect restaurant. The incredibly friendly staff went all out for us, and brought us champagne and tons of bread from the downstairs bakery. Everything was perfect, and I remember thinking that life simply couldn’t get any better. :) Mitch and I actually took Emma to Blue Ribbon Bakery this past Christmas, right before it closed, to relive the whole thing. That, too, was beyond special.

And with that, this girl is off to bed. :) I’m excited to spend a relaxing day with Emma, hang out with Shaheen after she gets home from work, and catch up with Lauren over dinner! In the meantime, though, any cute (or hilarious) date stories to share?!

Just remember the guy who texted about which cars were in the driveway. Can’t get much weirder than that… ;)