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Now that I’m single again, I’ve been out on a few dates. There are the usual venues: bars, restaurants, etc. But one date sticks out in my mind, because a) It was at six am, and b) It was on a bike.

I know, you are more than entitled to call me insane. Who goes on a date at six in the morning? On a bike?

Here’s the story: I reconnected with a guy who had asked me to go cycling with him before, and when he said he usually goes out on the weekends or six am, I decided to go bold and opt for an early-morning workout.

The next day.

Hey! Don’t judge. I’m really excited to be on the market again. No playing hard-to-get here.

So at six in the morning last Tuesday, I hoisted my turquoise Bianchi city bike on my shoulders and climbed down three flights of stairs from my new studio to the street. I wanted to impress without being over the top, so I wore an orange Stella McCartney Adidas top from Goodwill, an old pair of bike shorts, and a pair of Chucks from Salvation Army. (I had all this thrifty clothing because I participated in a challenge for Grist a couple weeks ago.) I had debated wearing a helmet, and then decided against it. Safety vs. Cuteness: Cuteness wins.

My date finally showed up (sans helmet also) and after a quick hug, he shoved off down the street with me following behind. We started up Third Avenue, but traffic was already crazy, so he led me over to First Avenue instead. We wove in and out of the bike lane, avoiding cones and trucks making deliveries. The sun rising over the East River was beautiful, burnt orange through the smog.

We talked some, but it was a bit awkward because we would often have to repeat ourselves over the roar of a bus or just the sound of the wind in our ears. He also found plenty of opportunities to make fun of me and my naive bike ways, as I cut him off and nearly caused him to crash. Oops!

We cut across town and entered Central Park, making a half loop. I dragged behind my date, since he was on a speedy racing bike. My bike only has three gears, so it will only go so fast. “It’s a recreational bike!” I told him. “What the heck is a recreational bike?” he said. I just shrugged and pedaled harder.

By the time we finished our loop, I was sweating and panting, and could hardly talk. But I felt awesome. This was why I had chosen a six am cycling date. I wanted to feel productive, healthy and adventurous. The guy was secondary.

I’m not tipping my hand on my thoughts on the guy (who knows if he’s reading this?). But I will update you if and when there’s a second date!

The Pros and Cons of a Bike Date

I enjoyed my bike date, with some caveats. Here’s what to know:

• Pro: You’re date will respect you for not being a diva.
• Con: You are not allowed to wear a lot of makeup. It will melt.
• Pro: Show off your butt in a pair of tight shorts.
• Con: Helmet head if you don’t feel safe without your helmet.
• Pro: Exercise!
• Con: Sweat.
• Pro: Novelty.
• Con: Not everyone has a bike in New York City. (Though they are available for rent.)
• Pro: No pressure for eye contact. Potential for awkward moments minimized.
• Con: Shouting to be heard, not much chance for meaningful conversation.
• Pro: If done early in the day, no expectation of a “nightcap.”
• Con: Involve alcohol at your peril.
• Pro: Avoid that moment when you’re date tries to hail a cab and you have to explain that cabs are kind of un-environmentally friendly, and would he like to take the subway or walk for a half hour to your destination?
• Con: Limits your choices later at night, since you have to either ride your bike home late or take the chance of locking it up out on the street.

 How to Do a Bike Date Well

My bike date was a little (or a lot) extreme. You don’t need to set your alarm for the crack of dawn to take your bike out for some romance. Here’s some tips for a romantic day on a bike around the city (Are you listening, boys? You’re the ones planning this!):

1. Plan it for a lazy Sunday or Saturday. This should be obvious, but I had to say it.

2. You don’t need to own a bike. There are places all over the city to rent bikes, from the Bike ‘n Roll in the Upper West Side stretch of Riverside Park, so the various bike shops dotting Brooklyn and Manhattan that keep a fleet.

3. Dress accordingly. For ladies: a pair of jean shorts that are on the long side (no booty shorts!) a fitted tee, and a pair of TOM shoes will keep you comfy and cute all day long. Or try a pretty sundress that is long-ish, and strappy flat sandals that will stay on your feet. Avoid white pants, as you might get grease on them. For men, I personally love the look of a button down (linen is the best) with the sleeves rolled up or a not-grungy tee, and cuffed pants with casual shoes. (See Downtown from Behind for reference.)

3. Plan your itinerary:

If you live anywhere on the West Side, take advantage of a beautiful and protected bike path, which stretches from 125th Street in Riverside Park, all the way down to the southern tip of Manhattan.  You can lock your bikes up and have a drink at the Boat Basin at 79th street or the Frying Pan at 26th Street; lean them against your table for some street eats and beer at the Lot on Tap underneath the northern tip of The Highline, or even have them valet parked for you at the New Amsterdam Market.

Make a couple loops around Central or Prospect Park (read more about the best parks in NYC). Pack a picnic in your pannier and throw your bikes down on Sheep’s Meadow. Pour some wine in your thermos to make it super romantic. Or, if you don’t have a big bike basket to carry stuff in, order a picnic from one of the restaurants or hotels that deliver to the park.

You have to take your bike across the Brooklyn Bridge at least once, if not every single weekend. Stop in the center and take lots of pictures like a pair of tourists. Then have lunch at O’Crepes, a few blocks over, or if it’s time for dinner, head south into Brooklyn Heights and sample one of the many delicious restaurants there.

If your date is in shape and is game, take your bikes all the way out to Coney Island. Spend the day wasting money on cheesy carnival games and rides, have a local Coney Island beer at one of the charmingly decrepit dive bars on the strip, and take photos together in one of the photo booths.