The Last Great Wingman

I’ll never forget that road trip on a cold and dreary late February weekend with my best friend of almost 30 years, even though it wasn’t really about me. Suffice it to say, my man Jeff was not in a good place. Worst of all, he had very little responsibility for the cloak of sadness he was now, unusually wearing.

The long weekend ahead started with an early bang just as we reached the New Jersey Turnpike when Jeff got a phone call. His credit cards had been fraudulently used and subsequently cancelled. Unfortunately, even though he had money, it was now more unavailable than his ex-wife and he had yet to visit an ATM.

When he told me what happened, I explained that I was pretty broke and couldn’t financially assist him, despite our longstanding plans to gamble and gallivant around Atlantic City for a random weekend in the dead of winter. Luckily, our friend Derek who was meeting us in AC could cover Jeff’s expenses.

Disaster avoided. Still, there’s no way I was coming up short again. Not on this weekend. This time it was different. Everything was different. Jeff’s pain was my pain and it ran deeper than ever.

If that wasn’t enough, his father also notified him that Jeff’s grandmother would likely pass away some time in the next few days and to be ready for that phone call.

I just knew it was my job to make it the best possible weekend for us, despite the flurry of terrible circumstances surrounding his life. “I know it’s not the type of place you go to expecting to meet someone you take home to mom, but you never know,” I told him.

He wasn’t looking to rebound, but I didn’t want him to rule out the possibility that he might meet someone cool there, especially now that he was free to do what he wanted. I just believed it could happen.

Friday night was a blur. As planned, we all felt rancid from poisoning ourselves the night before with too many shots. Me and Jeff had a long talk about his ex on the gusty balcony overlooking the frigid Atlantic Ocean. I cried. Jeff didn’t. It ended with me confessing, “I hate her.”

It didn’t help when we realized Bill had returned to the hotel room while we were on the balcony. Inviting Bill was a terrible decision based on the fact we all knew he was sniffing something in the bathroom and then ditched us so he could go cheat on his wife.

Jeff didn’t care much for Bill, especially after he called his wife and lied to her about his harmless night out with the boys.

Before we could fully recover, the sun had dropped in the sky and it was time to do it all over again. Friday was the night to party hard and Saturday was usually more low-key since we all had a load of responsibilities waiting for us on Sunday when we touched back down to reality.

This Saturday was going to be different if I had anything to say about it. I wanted to pump up the volume and so we did. It didn’t take long before me and Jeff downed a bottle of blue, 80-proof liquor that we will forever endearingly refer to as Smurf Piss.

I don’t remember exactly what we joked about as we drowned our sorrows, but I’ll always remember laughing them away together for those couple of hours. We got something intangible out of our systems and it was needed. We were now primed for a good night out.

Next thing you know, we’re at a small party in a hotel room at one of the casinos with some of Derek’s friends. Everywhere we went presented a new opportunity for me to try and spark up a conversation between Jeff and some women on the prowl, but we weren’t meshing well, so it was on to the main event.

And just like that, we were standing in the middle of a gigantic indoor pool party, surrounded by hundreds of people, flashing lights and booming beats. We were in the perfect place to enjoy the company of strangers and collectively forget about our problems.

Jeff was in the zone. I could tell he was in rare form and I was satisfied that I helped to get him there. Even if it’s ill-advised, guys frequently cope with divorce in the beginning by drinking it off, and we did a terrific job of that.

I felt great watching Jeff as he talked up a pair of girls by the grey stone bar. Then, the one in a black and white striped dress did something I hadn’t seen before. She suddenly took a step back and boosted herself onto the bar with her legs dangling off while Jeff made a series of funky hand motions that I often like to remind him about.

Unexpectedly, a new and interesting woman had just entered his world and I wasn’t even there for the assist. A few mixed drinks later, the girl who would become known as “the chick from AC” was leading Jeff by the hand around the party.

I could tell they were having a great time without me, so I decided to stay out of the way. But, I was still on best-friend duty, so I had to make sure she wasn’t an axe murderer as they stumbled around before finding an open space on a ledge bordering a garden.

She leaned in and kissed him. That was all I needed to see, so I left and did my own thing for a couple of hours before heading back to the hotel.

The next morning I said goodbye to Derek and barely acknowledged Bill before check out time.

On the way out of the city I picked Jeff up at a gas station. He looked awful and smelled worse, but he was super happy. It only took a minute to realize that he had a great time with this girl and that he genuinely wanted to talk to her again.

After all the crap he’d been enduring, for one fleeting moment, I saw my best friend feeling no pain. Mission accomplished.

We hit a fork in the road as we approached the turnpike. There was a median and we had to pick a side. For some reason, at the last moment, I decided to cut across several lanes of traffic to take the left side.

Not more than a few minutes later, a car travelling parallel to us on the other side of the median sprung into the air, flipped over and skidded on its roof in between the guardrails. I’ve never seen a more horrifying accident in-person.

I immediately pulled to a stop on the side of the road. Jeff bolted out of the car while I repeatedly tried to dial 911, but I couldn’t get through. When I got to the scene of the wreck, there were dozens of people who had stopped to help.

Jeff literally helped pull a baby out of the car, which was now laying on its roof with the windows shattered on all sides. A mother escaped next with a giant welt on the middle of her forehead and finally the father was helped out, still in a daze.

An ambulance soon arrived and we retreated back to the car. We were completely exhausted, both physically and mentally. “Give me a cigarette,” I scowled. We sat in silence for the next half hour, each trying to process a tornado of conflicting emotions.

I still don’t know why I decided to cut across so many lanes of traffic that day, but if I didn’t, we very well could have been in that same accident. I have to believe it was meant to be, just like Jeff’s romantic encounter.

Fast forward a few years, after countless hours on the phone, dozens of road trips between upstate New York and Philadelphia and Jeff is now married to the chick from AC — Maria.

That is why I just might be the last great wingman. On that fateful weekend, I didn’t have a dime to loan my best friend when he really needed it. I was also way more emotional about his divorce than he was and I invited a new guy on our trip that nobody liked.

But, what matters the most is that I positioned Jeff for success and that’s the true job of any respectable wingman.

While he was immersed in identify theft, divorce, death and doubt, I got Jeff to believe anything was possible.

At a time when I was seeing several of my peers experience broken marriages, I know in my heart that I was a critical piece to Jeff and Maria’s union.

Life has a way of reminding us that we just don’t know what will happen next, especially when it comes to relationships.

I’m truly grateful that I was able to be there when they met on a whim.

And if I were a gambling man, which I am, I’d bet it all that they’ll be together for the rest of their lives — the way it’s supposed to be.