The Time Cuba Gooding Jr. Tried to Steal My Date
A story from the dating apps.
*To those of you who are new around here, I mainly write education related pieces with the occasional fitness advice mixed in. But every once in a while I tell a dating story for the hell of it.
Whenever I visit my best friend in Chicago I inevitably find myself swiping away on the dating apps. Swiping while you're traveling is different from when you’re swiping at home. At home, I’m more selective. I pay attention to the women's interests, what do they do for a living, do they seem to like it, do they have a sense of humor, are they a horse girl? (I have a strict no horse girl rule.[^1]) The quality of the person matters to me. Don’t get me wrong, it’s still 90% pictures, but at home I read the prompts.
When I’m traveling though…I get addicted to the dopamine rush. A large metropolitan area like Chicago bombards me with hundreds of matches. I’ll swipe away as fast as possible, glancing at the first picture, swiping left or right from there. I’ll start a dozen conversations and see who’s the most interested in grabbing a drink. What can I say, volume matters when you only have the weekend to get laid.
On this particular occasion, I set up a date with a micro influencer. Her instagram is a perfect stereotype: around 11k followers, only bikini photos at various beaches around the world, and really killer captions like, “Florida Sunsets hit different,” and “Island Glow up.”
I was obviously in love.
I set up reservations at an Italian place with great reviews and told her I’d pick her up at 8. My fit included white Nike blazers, blue jeans, and a crisp white T. Most importantly, my buddy let me borrow his ludicrously expensive wool jacket. It’s stylish, reeks of finance money, and fools you into believing you can tackle any social situation life throws at you. When the time came I hopped in an Uber Black and went to pick her up.
The first time you meet someone from the internet is a telling moment. When you swipe on the apps, you’re making a judgment based on the 6 best pictures they represent themselves with. When you meet in person, it’s different. There’s no perfect lighting to save you, there’s no flattering angle, there’s just the confidence you project and what you actually look like.
She was absolutely fucking gorgeous.
Dressed in a mob-boss-wife fur coat and a beige dress that clung to her figure, it was clear her pictures didn’t lie. She had all the curves a boy could dream of. Thank god I was wearing my buddies coat. I walked up with a smile, introduced myself with a quick hug and a kiss on the cheek, and went to the Italian place from there.
There’s a certain thrill you get when you walk into a restaurant with a hot date. People’s eyes flit sideways for a glance, the service treats you like a VIP, and the crowd wonders what the hell you do for a living. Whenever I realize it’s happening I crack a grin. It’s my own private joke on the world - I teach.
After enjoying the elevated status, we sat down to dinner. It was time to figure out if she was the real deal. When I say “the real deal,” what I mean is is this someone I could possibly fall in love with? Do they have a vivacious love for life? Are they following their dreams? Do they have a love for dark humor? Are they tough? Can they make fun of themselves? Can they laugh freely?
Within 5 minutes I knew she wasn’t what I was looking for.
The moment we sat down she started positioning her wine glass in the candle light so she could take a picture for her instagram story. She ordered an absolutely divine Cacio é Pepe that received ten different angles from her phone, and about three bites. When she went to the bathroom she came back with a mirror selfie. She struck me as a woman obsessed with how the moment looked, rather than living in the moment itself.
I didn’t mind.
I have two basic rules when dating. Rule #1: Have fun. Rule #2: keep your eyes peeled for “the one.” 99% of the time they’re not the one[^2], so when that happens, you revert back to Rule #1: have fun. The rules keep you from burning out from the dating game. With the right mindset, every night has the possibility of becoming a memory, even when you’re not playing for keeps. So have fun I did.
I teased her about her phone use. I joined in on taking pictures of the food and told her I clearly took a better photo. Then I’d show her the picture, and it would be a picture of her taking a picture of the food. We chatted about what we loved to do. I told her about the kids I teach, she would talk about her travels. I’d joke that if I ever traveled with her I’d have to make sure I packed more bikinis.
If this sounds boring, I can assure you it's not. I enjoy flirting even when I know the person I’m flirting with isn’t what I’m looking for. Who’s to say you’re not allowed to enjoy the moment. Lingering eye contact and finding ways to intertwine fingers over bowls of pasta is something I’ll always love.
When the meal came to a close we were both a smidge tipsy and having a good time. Anytime I have a date I’m excited about, I always have a second location in mind. It’s a great litmus test. If someone agrees to go to a second location with you, you have real confirmation that they actually enjoy your company. When a girl agrees to go on a date with you, they’ve signed up to give away no more than an hour of their time. Anything after that is a choice they make in the present.
I asked her if she wanted to go to a place called The Redhead Piano Bar. I knew it was a fantastic location because I had spent the night before getting drunk with my buddies and sending ludicrous song requests to the piano player - the best of which included a hilarious rendition of Snoopdog’s “Drop It Like It’s Hot.”
She hesitated. I knew it was a long shot. It was a Tuesday night, and while I was enjoying February winter break, she had work the next morning. She also knew I was hopping on a plane home the next morning. It’s one thing to go out and have a guy pay for your pasta and wine, it's another thing entirely to go out to a bar with him when he’s leaving the next morning.
I told her not to worry if she couldn’t, I understood she had to work. It's a rule when dating. Never pressure, always leave space. You only get to offer the opportunity, they have to choose to take it. I figured the night was over, and it had been a damn good one.
Then she surprised me and agreed to go.
Well here we go.
The Redhead Piano bar is a double whammy of rich ambience and fantastic live music. Dark leather and dark wood surrounds you as you sip cocktails and listen to live piano-singer performers. The woman behind the keys that night was beyond talented.
She could play anything the crowd wanted. Pop music, broadway musicals, rock songs, happy, sad, slow, fast, she could do it all. Even better, she knew how to handle a crowd. She’d heckle the old men, and encourage the woman to come closer to the piano. She’d grin in delight when someone made a song request that she liked, and she’d say “what is this!?!” in joking exasperation on the rare occasion where someone requested a song she didn’t know.
My date and I had a great time sitting back watching the performer work. The crowd loved her, and it was easy to see why. For the price of a cocktail, we were watching world class talent entertain on the fly. For fun I ended up requesting Backstreet Boys “I Want it That Way,” and while I sang it out loud, both the piano player and my date had a laugh. A good night was turning into a great one.
Then, while I was working my way from tipsy to drunk, a man entered the bar and turned his back toward the crowd to take off his coat. No one would have noticed, except when he entered, the piano player suddenly stopped singing mid song. She kept playing on the keys while she announced, “ladies and gentlemen, you may or may not know this, but a VIP has entered the premise.”
The man still had his back turned to most of us as he approached the piano player. It was clear they had rapport. She said, “give me a song, anything you want. I’ll play it right now.” The man moved his head from side to side trying to figure out a song request, and then said, “Journey.” The piano player immediately started banging out the opening chords to “Don’t Stop Believing.” Then the man finally turned around to reveal himself to the crowd.
It was mother fucking Cuba Gooding Jr.
The bar went nuts.
Watching him move through the bar was like watching charisma personified. One second he was flirting with the 50 year old ladies in the corner, the next moment he was back slapping a guy he didn’t know and taking a selfie with him. Besides the piano player, it was clear Cuba didn’t know a single person there, and it didn’t stop him for a second from introducing himself to everyone.
As Cuba worked his way down the bar, he finally got to us. Watching him slightly sway I realized he was completely hammered. His introductions to random people suddenly made a lot more sense. Mockingly playful, he opened his eyes wide and pointed at me. Then he pointed at her, then back to me. Then he said, “Mah man, don’t fuck this up.” We both roared with laughter and I pulled him into a bro hug. He kept moving down the bar saying hello to people.
Clearly impressed, my date asked, “Who is that!?” I excitedly told her it was Cuba Gooding Jr. When she shook her head to say she didn’t recognize the name, I started listing some movies he was in. Radiohead, Crash, Jerry Maguire - she didn’t know any of them, but still watched him with interest. On the inside I had to laugh. This is why men chase status.
As the night moved on, we eventually joined the crowd in front of the piano so my date could take some insta stories of the performer. She was exercising her craft to perfection, getting the crowd to drunkenly sing Billy Joel, and creating a dance party by playing Taylor Swift’s, “Shake it Off.”
Meanwhile, Cuba was sitting at the side of the piano, clearly drunk, casually crumpling up 20 dollar bills and shooting them in the tip bowl - mostly missing. He didn’t appear to be meeting anyone there, and despite his outrageous entrance, now that he was seated, he didn’t look like he was actually having much fun. He looked old, and tired. I had a drunk contemplative moment where I wondered if fame just made you lonelier.
However, the empathy drained away when I noticed he kept shooting glances at my date. He’d glance our way and then look right back at his drink. Internally, I had a laugh. Every guy has had the experience of sneaking looks at the hot girl at the bar, regardless of whether she’s with someone or not. Apparently, fame doesn’t change the habit. I almost felt smug about it, but when he got up to go to the bathroom he casually passed us and my date went out of her way to assure him that we weren’t together.
Ouch.
It might have stung more, but as the night had worn on my charm was running out of battery, and I could tell my date was getting ready to go home with nobody. She had had three bites of pasta at a world class restaurant. She had seen a world class singer in a world class bar. She had received attention from a famous guy she didn’t know. All had been recorded on social media. Her 11k followers would see her do fantastic things in fantastic places. In her book, the night was done.
Much as I would have enjoyed getting laid, I knew it wasn’t going to happen when the piano player burst out into a rendition of Whitney Houston’s “I Wanna Dance With Somebody,” and she didn’t dance. I smiled at her, and tried to get her to move while the bar attendees and I sang the lyrics, but she just smiled at me and slightly shook her head. Who doesn’t dance to that song!?!
When she told me she was getting ready to call an uber, I wasn’t all that surprised. I told her I’d walk her out when the time came. At least I hadn’t blatantly lost my date to a celebrity, though I really wouldn’t have blamed her. It is Cuba Gooding Jr. after all.
My final interaction with the movie star came two minutes before her car arrived. Cuba was glancing our way again, and when he saw I had caught him staring he gave me a mock serious face, pointed his middle finger and pointer fingers at his own eyes, and then pointed them at mine. The universal gesture for, “I’m watching you.”
I looked at my date and said, “Hold here for a sec, I need to have a word with Cuba.”
I walked right up to him with my own mock serious face - wide eyes and a slight smile. Generally speaking, I’m fairly confident, but with a couple of drinks I can do anything. I said, “What do you think is gonna happen right now?” We locked eyes and I swayed my head gently.
The tension built as we continued to stare down one another.
Then Cuba barked out a laugh and pulled me into a drunken hug. As he pulled me in, he grabbed one of my biceps and said into my ear, “you remind me of my son.” Then we let go and had another laugh. As my date and I walked out I gave him a slap on the back.
The uber rolled up and I shared a brief kiss with her. I told her I’d love to see her if she ever came to New York. She lied and said she would.
Down $350 and definitely did not get laid.
But what a fucking night!
[^1] If you’re wondering why no “horse girls,” here’s the reason. A horse girl will never love you as much as they love their horse. You are a far far distant second place. If they have a dog, then you’re third. And a dog isn’t like a horse. You can make friends with the dog. You can be part of that dog’s world. A horse is different. A horse girl will travel to see her horse, groom her horse, and ride her horse. In the meantime you sit there wondering if she’s thinking of you while she’s using her limited free time to hang with her horse. She’s not.
[^2] I’ve met exactly 2 girls where I decided I was ready to trade the freedom of being single for the joy of a relationship…but those are stories for another day.
There are so many sad stories of past-their-prime celebrities, crashing bars and stealing girlfriends. Bob Crane used to ask the bartender to turn the TV to "Hogan's Heroes" re-runs so the patrons would recognize him. I'm surprised Cuba didn't make a request to the piano player to do "Secret Garden".