July 23rd, it was my friend Jackie’s birthday party. A small group of eight met up before a night of drinking to get dinner. I was a bit out of the circle of people, I recognized some of the people from previous events, but didn’t really know any of them. One guy in particular that I thought I knew, but obviously didn’t was Adam.
At some point in the dinner, I asked Adam, “Weren’t you that guy from two New Year’s Eves ago?”
He was absolutely confused, “No, I wasn’t in Chicago then.”
Jackie butted in, “Who are you thinking of? Was it…” She then started to ramble to list off friends of hers it could have been.
I explained, “Good, glad you aren’t him. He kept staring at my tits the entire night and was a total prick.”
Adam laughed, “Thank god I’m not him then.” He smiled at me, I smiled back. At least I didn’t make a complete fool of myself quite yet. Adam is cute, brown eyes, dark hair, clean-cut, nice build. He is former military and conservative, not quite my type, but I was already captivated by this flirtation we have started. It was still early in the night, so we did some coy looks across the dinner table.
After dinner, we all made our way downtown to the bar. When we arrived, we were joined by several other people. We took over a pretty large section of the Chicago Athletic Association’s game room. Adam sat and ordered a drink, I went off to the restroom. When I got back, the only seating was the opposite side of the section we took over. I sat down, but it wasn’t long until Adam and I started making flirtatious eye contact.
Once the first round of drinks were consumed, everyone was ready for some games. Several of the people went straight for pool, and a group of us made our way to bocce ball. A game of four on four, girls versus boys. Lo and behold, Adam and I both were playing bocce ball. In between turns, Adam made an effort to talk and flirt with me.
As the night progressed, more and more people joined. Adam tried to get me on my own, he insisted we should order another round of drinks at the bar and check out the other side of the game room to get away. When we got to the bar and ordered our drinks, another friend of mine followed and was trying to catch up with me. I gave her a look like, “Dude, I’m occupied right now.” She quickly caught on and walked away.
We then grabbed our drinks and found somewhere quiet to chat. He was sweet. A bit reserved and quiet, had a cadence you would expect to hear out of an old movie, but this only lured me in more. Not more than 30 minutes later, a friend of mine interrupted to tell me she and a group were headed to Chinatown. While I went and said my goodbyes, Adam got pulled off to play shuffleboard with Jackie and some others.
I drank and watched from the sidelines, Adam and I kept making eyes, so I wasn’t really paying much attention to the game. As the game wrapped up, the birthday girl and the few others that were left took over foosball, Adam and I found a chess board to play. We chatted and played and flirted and I totally kicked his ass. As our game came to an end, Adam’s friend came up and summoned us to the bar to take shots with everyone.
One shot down. “Cheers to Jackie!” Another round was poured, without hesitation, we were all grabbing our second shots. “Happy birthday!” Two shots and four or five drinks in, I was definitely starting to feel it. It was about 1:30am, Jackie was still going strong, so she said we should go to Mindy’s, another Chicago Athletic Association bar on the top floor. We made our way up, everyone ordered drinks and sat at the bar, and I grabbed a water and sat on a couch by the window to chill for a bit.
I sat there watching the lighting in the distance flicker beyond Millennium Park. Not long into my reminiscing, Adam joined me. We sat in silence for a minute. It was nice. To break the silence, he asked, “How would you feel about walking along the lake once we leave?” I was exhausted and a bit tipsy, but I didn’t want the night with Adam to end quite yet, so I agreed.
An hour or so later, they announced last call. I was ready to leave to walk with Adam, but had to wait to make sure Jackie was ok. She was pretty hammered and was flirting with the bartender. He asked for her number, she gave it and lingered. I had to pull her away, the bartender smiled at Jackie as we left.
We headed out, Adam and I walked together a little behind as the other three remaining souls were a few feet ahead. His friend was on a mission to get us all to the next bar or somewhere we could keep drinking. Adam looked at me and said, “Let’s ditch them.” I agreed. At the next crosswalk, the three ahead of us walked straight and we bolted right and crossed the street to cut through Millennium Park.
As we approached the park entrance, we were quickly stopped by the guard, “The park closes at 11pm.” We turned and walked along side the park towards the lake instead. We walked up Randolph, I knew all along we were going the wrong way to the lake, but I let Adam lead. He eventually realized we were on an upper level street. There was no way to the lake, at least an easy route from where we were at. He asked, “How adventurous are you?” I laughed, although I was in a dress and flats, I am still always up for an adventure. We hopped a few fences, and found our way to Lower Wacker, then to the river walk. Finally, a clear route to the lake.
We walked and talked and laughed and flirted. He’s very well mannered while I have a sailor’s mouth, a weird mix to say the least. I called him out and said to loosen up, he said it just takes getting to know him before he fully unleashes reveals that he is just as vulgar as me. I don’t know if I fully believe this.
The river walk merged into the pier and docks just East of Randolph. We walked along the pier and found our way to the end, the last dock was several police patrol boats, then there was a cement barrier separating the docks and the lake. We faced more fences. Adam asked, “Are you still feeling adventurous?”
“Bring it on.” I replied. He swung his leg around the fence, lifted himself above the water, and reached his leg to the cement ledge. I followed, but being shorter, plus in a dress, this fence proved to be a little more difficult than the ones from earlier. I quickly realized the way my dress was stretching over the side of the fence, it was making it difficult for me to spread my legs far enough to reach to the cement barrier. Adam saw my struggle, and reached his hand out to pull me over.
We continued our journey along the cement barrier. As we walked further and further, suddenly swarms of seagulls flew up above us cawing. It was actually quite beautiful, hundreds of white birds flying overhead alongside skyscrapers on one side, the lake on the other. We approached the end of the barrier and leaned against the wall. Adam created a story about a military man and the lighthouse in the distance. His voice was soothing and somehow blocked out the noise of the seagulls.
As his story came to an end, he looked me in the eye, I smiled. He smiled back. My heart started to race a little, he leaned in and kissed me. We locked lips, his hands on my waste, my arms wrapped around his neck. A perfect romantic moment you’d expect to see in the movies. We continued to make out for several minutes. He pulled back, smiled at me, and I smiled back. We were quiet, but it was a comfortable silence.
“Do you want to go to the beach?” he asked to break the silence.
I agreed, but then I added, “First, I need to pee.”
He laughed and led the way back to the pier, helping me back around the fence. We walked back to the start of the pier and luckily there were bathrooms that were somehow still open at 4:30am. I went in to pee, he stayed out and waited. When I came out, he asked if I wanted something to drink. I laughed, “Sure?” confused as to where he would get us drinks. Turns out not only were the bathrooms left unlocked, the patio by the bathroom, although gated off, wasn’t too hard to squeeze past the gate and get to the fridges which were also unlocked.
He grabbed us each a sprite, then we found our way to the nearest street to call an Uber. He pulled me in and held me and kissed me and we waited for our ride to the beach. We got in the car, headed north, and were dropped off near the beach entrance. The entrance was blocked off, another place that closes at 11pm. We started walking down Montrose away from the beach, and he said, “Well that was kind of a fail; where would you like to go.”
He had told me earlier that he lived near Montrose Beach, so I said, “We could go to your place.”
Adam hesitated, then revealed, “I would say yes, but I actually still live with my ex girlfriend. We’ve been broken up for two months, I’m the one on the lease, she’s refused to move out, and I wasn’t putting up a fight. My lease ends at the end of the month, so I’m moving out next week.” Red flag… but there’s always some of those.
Not really sure if I should end the night, but still kind of tempted to keep going, I brushed if off and said “That’s gotta be tough.” I paused, “Well, we can still go back to the beach, just not use the main entrance.”
We walked back, but headed south away from the entrance and cut through the trees and grass. As we scurried through, Adam grabbed my hand as to guide me through faster. As we exited the tree covered area, we slowed down the pace and continued to hold hands as we walked. We ended up on a hill. At the top, Adam pulled me in yet again. He’s very affectionate, which I usually like, but I felt a little off with all of this. He seems way to proper for my taste, but it was still very sweet so I went along.
After a prolonged embrace on the hill, I pulled away and started to head towards the beach. He followed. When we got to the beach, we sat on the ledge just before the sand. He put his arm around me, I leaned up against him, putting my head on his shoulder, watching the waves flow in and out before us. We chatted some, but the night had us both exhausted so we mostly sat in silence, taking in the view in front of us. An hour passed and we watched the sun rise.
As daylight got brighter, I was quickly reminded of what time it was. I told him I should probably go home. We walked back towards Montrose, I called an Uber home. He waited with me and held me and kissed me some more. I was torn. At this point I was a little turned off by the fact that he lives with his ex still, but I enchanted by his affection. It seems like even the most well mannered boys still have at least one red flag, and this was a big one. My Uber pulled up, we said our goodbyes, and I headed home. As soon as I got home, I went straight to my bed and passed out until 3pm.
I woke up to a text from Adam. Now what to do with it?