Two friends and I were plotting on how we were going to spend New Year’s Eve. We’d narrowed it down to a couple of clubs and got ready to go. Our hair was done. Our outfits were carefully chosen. We were ready to hit the Chicago streets and enjoy ourselves.

Shortly after arriving at the club, there was a guy who took a particular liking to me. I thought he was a bit of a goofball and trying way too hard, but he was funny and attractive. Although I mingled with my friends, I often ended up dancing and drinking with him. I wasn’t sure he was a long-term match, but he was cool enough to bring in the year and hug at midnight.

When the fireworks were out, the “last call for alcohol” announcement came over the loudspeaker and the doors opened, we all went our separate ways. It was a fun night, but I didn’t think much about him afterward.

Was it a good date or beer goggles?

When beer goggles make you less confident in your date

A day or two later, I noticed a text from an unfamiliar number during my lunch break. The exact message is foggy to me, but it basically translated to, “I want to see you when I don’t have beer goggles on. I don’t know if you’re cute or not during day hours.”

It was the New Year’s Date guy. I laughed and responded that I was at work. He asked if he could pick me up from work to chat for awhile. I agreed.

Now imagine my surprise when I stepped outside to see two men standing outside of the car he said he was in. (Note from a much older, much wiser woman now: Do not, I repeat not, get in a car with two grown men you barely know. I was operating off of optimism about daylight hours and him “seeming like a nice guy.” I would tell my younger self this could’ve been very dangerous and to take the el train instead.)

I looked from him to his third wheel friend and back again, waiting on an explanation. New Year’s Day date said his car was “in the shop” so his friend came with him. I raised an eyebrow. Why does his friend have this much free time? New Year’s Day date blurted out, “Nah, I really just didn’t know if you were crazy so I brought my friend as backup.”

I laughed. I could respect the honesty, and this guy was a handful. He got in the backseat of the car so I could ride shotgun. (Note: I’ve been informed by several guy friends that if a guy makes you get in the backseat, he doesn’t think you’re important. However, this was a weird setup to have to constantly turn around to talk to the person who came to see you. And me sitting in the backseat with him would’ve felt like a Lyft ride.)

When a third wheel turns into the better option

I didn’t realize I liked his friend more than I liked him all at once. I started off exclusively talking to the guy from the New Year’s Eve party, but we were having the kind of pregnant pauses one has on a date that’s not going so well. We just didn’t have much to talk about without a bartender, music blasting, my friends twirling me around and random people doing their best dance choreography.

His friend started talking to me. Then he kept talking to me. Before I was fully aware of what was happening, I was halfway home and solely talking to his friend. Then I took a good look at the driver and realized he was absolutely gorgeous. (I was too distracted by there being two men instead of one and New Year’s Day date not forewarning me ahead of time. I saw his friend from the outside of the car, but from the passenger seat, I could size him up.)

The third wheel had a nice build, smooth skin, bright smile, and was fashionably dressed. He was a good driver, funny, had the kind of baritone voice reserved for children’s books, and was noticeably charismatic. If I had to rank the two men (with “1” being the worst and “10” being Idris Elba/Michael Ealy), my New Year’s Day date was a 6.5. His friend was a 9.

Meanwhile, my New Year’s friend had grown quiet, just listening to the two of us easily talk about a little of everything while cruising down Lake Shore Drive (recently renamed Jean-Baptiste Pointe DuSable Lake Shore Drive). He may as well have just dissolved into the floor rugs; I forgot he was there.

This is Lake Shore Drive (recently renamed Jean-Baptiste Pointe DuSable Lake Shore Drive after the Chicago founder) (Photo credit: Matt Kieffer/Wikimedia Commons)

How to gracefully handle dumping your date

I wasn’t quite sure how to handle this situation. On one hand, he shouldn’t have brought his friend in the first place. (Call me superficial, but he especially shouldn’t have brought a friend who looked like this guy.)

On the other, he didn’t bring his friend with the intention of either of us hitting it off nor did either of us know we would hit it off. Our conversation flowed easily. We talked about everything from him being a pianist to my first published novel. No one has these kind of thought-provoking talks and easy chemistry at a nightclub. That usually happens at brunch hours.

Still, when he stopped in front of my apartment, I thanked them both for the ride, made no mention of talking to either of them later, and just assumed I’d never see them again. I honestly had no interest in seeing the New Year’s date again anyway. Who was he going to bring with him next? His dog? (In all fairness, if he brought his WingPet, that would’ve gotten him some extra fluffy brownie points.)

When the friend pursues his friend’s date

Within a couple of days, I answered my phone and heard the sound of that children’s book voice. It was his friend. My jaw dropped. It turns out that his friend was honest with New Year’s Day date and said that he was into me. He wanted to know if it was OK to pursue dating me without causing conflict between the two.

I thought that was honest and messy-free. I had not called nor texted New Year’s Day date after the DuSable Drive ride, and he hadn’t contacted me. And there was no way for the friend to get my number without assistance. I was both relieved and flattered.

Was I wrong? When I told this story recently, a guy quipped, “I guess I have to keep you away from my friends. You’ll be trying to date all of us.” I raised an eyebrow. I looked at it differently because it was vice versa. His friend made that next move, not me. And sometimes, in the dating world, you just never know who you’ll hit it off with.

Life is in the driver’s seat; I’m just here for the ride.

FASCINATING