This past Saturday night my wife and I went out with some friends for a low key evening in Pittsburgh’s Strip District. The night started off just like any other Saturday but where it went was something out of a movie, like The Hangover. I’m writing about this to share the story but also for my personal memory as the further we get from the night, the less I will remember. Also, because I did not get permission from anyone, I will be changing all the names as to not identify people.
My friend Heather and I were texting back and forth about hanging out on Saturday and never really decided on anything. After her husband Chris got home from work she mentioned about having a herf at a local cigar lounge. Most of them in the area, including a new local spot nearby, close in the early evening. Heather recommended a fancy spot in the Strip District called Cioppino which is a restaurant with a Gatsby-style cigar lounge in the back. We decided on a time and had to change because this place has an unspoken business casual dress code. I packed up my own cigars and accessories before we left, I brought two different sticks because I wasn’t sure what I would be in the mood for later that evening. We left the house around 8:00pm, said goodbye to the dogs, and expected to be back within a couple hours.
When my wife and I arrived in the Strip District we were expecting to have to valet the car, but to our surprise there was a parking garage directly above the restaurant. We found a spot on the second floor right near the stairs we needed to descend to get to Cioppino. It was a warmer night than a usual late January evening so I decided to leave my coat in the car which would save it from cigar stench. At the bottom of the stairs we had to brave the cold wind for a moment to walk around to the entrance of the restaurant. When we walked inside we were immediately hit with the smell of fresh seafood and I remember thinking, “There’s a cigar lounge in here?”. I quickly greeted the host mentioning we were meeting friends but we weren’t sure where the cigar bar was. He replied eagerly, “Let me show you since most people get lost on the way, follow me”. We literally walked around the corner and straight through a door labeled “No smoking beyond this point”. I wasn’t sure how anyone would get lost on that treacherous journey. Walking in we were hit with the unmistakable aroma of cigars burning, but pleasantly surprised at how nice and welcoming the lounge was. After finding a table for four we sat down and ordered two diet Cuba Libre drinks and waited for our friends.
Heather and Chris arrived a few moments later and we start to enjoy our chosen stogies for the night. I went with a “M by Macanudo” which is a Columbian coffee infused cigar with an Indonesian Bezuki wrapper. This was very smooth and enjoyable. As I sipped my drink and smoked my cigar we all traded pleasantries and discussed how our respective jobs were going. Directly behind us was a couple who were obvious cigar newbies. They ordered two expensive large cigars and I thought to myself “Good, I’m glad they’re jumping right into it”. Later on, Chris told me to carefully look behind me and check out that same couple. As I glanced over my shoulder I immediately noticed the problem. Sometimes cigar manufacturers include a thin wrapper around the outer leaf made out of cedar. This is intended to protect the outer leaf as well as maintain the bouquet of tobacco aromas. Normally, you use this cedar wrapper to light your cigar or remove and discard. The couple behind us smoked their entire cigar with the cedar wrapper attached. That had to have been a bad experience. The cedar taste must not have deterred them because after they finished those they went back for two more.
About an hour and a half passed and I decided I was going to smoke my other cigar before the lounge closed up shop. At the table adjacent to us were two men having a good time but were clearly from out of town. One of the guys saw Chris’ travel humidor and began to engage him in cigar talk. They shared what they had with them and opted to trade each other cigars. Both Chris and this stranger are very outgoing and introduced everyone to each other. We all began talking about work, travel, and cigars. The two guys, Shawn and Brad, were naming all the places they’ve been and where to get the best cigars. Curious, my wife asked Shawn what they did for a living since they got to travel for work so often. Shawn responded, “well… you guys don’t seem like terrorists so we can tell you, we’re Federal Air Marshals”. We all gasped in shock because we weren’t expecting that as an answer. I’m not normally one to engage in meaningless conversations with strangers, but I remember thinking “Ok, these guys are actually interesting”.
The six of us probably chatted for an hour about cigars, whiskey, and air travel. Stephanie was in a daring mood so she was trying a new flavor of Jameson Irish Whiskey she hadn’t tried before. After that, Shawn ordered her a glass of some fancier, more expensive, Jameson for her to try. While it was nice of him, I felt like he may have been trying to hit on her. Shawn and Brad were wondering where they should go next since the night was still young. Chris half-jokingly said they should go to a gentleman’s club right up street. Shawn seemed all for it, but since it was late the four of us were going to turn in for the evening.
After more conversation and planning Chris offered to drive our two new friends to the gentleman’s club since they didn’t have a car. Chris also happened to know someone who worked in the club that would allow us to get in for free instead of paying the steep cover charge. Feeling a bit adventurous we all agreed to go along and see where this would end up. Personally, I love to say “yes” to things as much as possible, within reason, and that’s how situations like these arise. We quickly paid the bill, paid for parking, and exited the garage to head down the street. Upon arriving at Cheerleaders gentleman’s club they had mandatory valet parking for $8.00. Because I had no cash, I had to get my wife to pay for it and she brought me cash and we headed inside. We proceeded through the metal detectors and past the cashier, thanks to Chris’ friend, into the club. I went to get some change for the large bills of cash we had and by the time I turned around, Chris was sitting in a very large VIP area. I walked over and said, “is this for us?” He replied, “Hell yeah this is for us!”
This is when the night quickly escalated. Three of us ordered more diet Cuba Libre drinks and I headed to the restroom. Upon my return, instead of a glass of Captain Morgan and Diet Coke on the table I found an entire bottle of Captain Morgan. Shawn had purchased this bottle service for us. We were astonished and extremely grateful. Shawn and Brad continued to drinks glasses of Jameson whiskey, piggybacking on the ones they had at the cigar lounge. A nice middle-aged women came to our VIP area and offered neck massages for about $20. Earlier that morning I attended a yoga class so my shoulders were quite sore. Chris went first and gave his recommendation on the massage so I signed up to be next. It was a pretty good neck massage but it kind of creeped me out being massaged in a gentleman’s club VIP booth. After the massage we toasted to meeting new friends and continued to work on that bottle of Captain Morgan. If you have ever been around people that are drinking, it seems all they want to do is have you drink more with them. As the designated driver for my wife and I, I was making sure I wasn’t drinking too much. To not be a party pooper, I would drip a few drops of rum into my glass and fill it the rest of the way up with Coke. This worked most of the time until one of the drunken guys would make a drink for me. I must have had seven or eight glasses of Diet Coke that night.
If you ever been to a gentleman’s club or a strip club you may have experienced the sales tactics of the women who work the floor. They will continually come up to you and ask for drinks, dances, or whatever, just to make some money. I appreciate their hustle, but I will not be fooled into spending money on them. One young girl stopped by our area and started giving Brad the sales pitches. He wasn’t drunk enough to fall for it and she quickly left. Chris and I were the only sober ones in our six person crew so we commented about how crazy it was that we ended up here. Shawn would periodically make his way around the club checking out the girls, giving tips, and buying drinks. Meanwhile the four of us pretty much stayed in our VIP area, standing around drinking except for the several trips to the restrooms. Later the same girl who was working on Brad came back and must have sweet talked him just enough for him to agree to go in the back with her. Now I’ve been to a few bachelor parties and know what goes on back there (nothing illegal), how much it costs, and how long it takes. Brad quickly came back within two or three minutes. I knew something was wrong when I saw him walking back and then I saw his face. He couldn’t really speak clearly, whether he was in shock or just intoxicated, but all I really got out of him when I asked what happened was, “I felt bad for her, she’s so young, I don’t know, I just felt bad for her”. At this point I urged everyone to cut him off from drinking but this fell on deaf ears of his travel companion. The Jameson shots kept coming out in succession.
In the booth next to ours was a large group of young ladies, I’d say about 15 of them piled into a small sitting area. We immediately thought bachelorette party, but as the night went on, they didn’t exude that vibe. Finally, Chris asked one of the ladies what they were celebrating and how we immediately thought it was a bachelorette party. She scoffed at this notion and proceeded to explain how she used to work here and was working somewhere else, but is leaving that job, so they were all out celebrating her last day. Brad became completely interested in this girl and began talking to her and flirting. At one point Shawn, Brad, and the neighbor girl (I never caught her name) were playing a game where they bet shots on guessing age and ethnicity. She lost and had to take two shots, but I could tell she was nervous about taking drinks from these guys. I didn’t have any reason to suspect foul play so I didn’t interfere. At this point I lost track of how many Jameson shots these two guys had. Shawn was still functioning, but Brad could barely stand.
Shawn and I had some great conversations about being a Federal Air Marshal and how that impacts his home life. Without giving away too much personal information, Shawn is a second generation Air Marshal who has been serving for over 15 years.
Brad was still over talking to our neighbor who didn’t want to leave her party, but was interested in ours. At one point I saw him climbing over the wall between our areas, knocking over some glasses, and falling into the booth. Some of us thought, “He’s going to get us kicked out of here”. Our bottle of rum was about 1/4 full and we were ready to hit the road, it was 2:00am at this point. Shawn convinced us to stay and finish the bottle while he ordered up some more shots. I was standing by the railing, which separated our VIP area from the main bar area, holding my drink when two girls approached me. They reached out to shake my hand so I switched my drink to my left hand, wiped off any condensation on my jeans and shook their hand. They noted how cold my hand was and I explained it was because I was holding my drink there. They then started to comment on how big my hands where and made insinuating facial expressions. I know this as one their sales tactics, so I played along. One of the girls said to me, “you have really big hands, that must mean…” and she reached for my crotch and said “do you mind?” I said no, but motioned behind me and said “You’ll have to ask my wife.” They immediately said “oh no!” While quickly turning and walking away. I laughed and walked behind me and told the story to Stephanie and Heather. Those two were pretty intoxicated at this point so they laughed along.
Another nice young girl approached Brad, who at this point was swaying while standing up and had a glossed over look on this face, with the usual sales pitch. Shawn saw this and immediately came over, handed the girl $200 to buy him a few dances. As they walked away Shawn yelled “Happy Birthday Brad!” And we all joined in knowing it was definitely not his birthday. The girl escorting Brad away replied “Oh, that’s why you guys are out celebrating, happy birthday!”
We were wrapping things up and polishing off our drinks when we noticed Brad had been gone a lot longer than his previous trips to the champagne room. Shawn mentioned about them getting back to their hotel near the airport as they were flying out tomorrow. An Uber ride from the Strip District to the airport was going to cost over $80, so Chris offered to give them a ride much to Heather’s chagrin. Shawn then disappeared and the four of us collected our thoughts on how crazy it was that we were there and how all these drinks have been free. At one point, we were concerned that we have been scammed and could be stuck with the bar bill. All of a sudden we see Shawn talking to a police officer near the entrance. He waved us over in a way that suggested it was time to go. When we arrived at the entrance area, which also happened to be where the entrance to the champagne room was, Shawn was having a friendly chat with the police officer and Brad was standing there expressionless.
We walked out of the club, said our goodbyes, and thanked our new friends for the great night. They got in the car with Chris and Heather and headed towards the airport and Stephanie and I got our car and drove home.
Sometime later Heather sent me a few messages about what happened before we left. As of writing this I’m still not sure what happened exactly. Allegedly during one of Brad’s final interactions with the dancer, he removed his penis from his pants to insinuate an illegal act. This is a huge no-no for places like this, and most public places to be honest. Luckily he was not forcibly removed from the club or arrested. There could be more to that story, but it sounds pretty believable to me.
All in all it was a great night with old friends and new friends. No one got hurt (or arrested), everyone got home safely, and lived to tell the story. You’re probably reading this thinking “that really wasn’t that bad or hard to believe” but to us it was. Normally we have quiet adult evenings with our dogs, this took us out of our comfort zones and we had a good time. Hopefully we run into Shawn and Brad in the future, but if not I wish them the best luck!