On Tuesday night—right after we finished stalking Ben Stiller, who was filming a scene for Little Fockers at the intersection of Wrightwood and Dayton—my brother, Lee, and I headed to Rebar at the Trump for a media tasting of the lounge’s new fall cocktail menu. I’ve been cheating on Rebar with the 16th-floor Terrace since the latter opened over the summer, and I was curious to see if my old spark with the former was still alive. (Despite the high risk of tourist run-ins at Trump, I am deeply in love with the river views from both Rebar and Terrace.)

Lee was visiting from the tiny coastal enclave of Vero Beach, Florida, where he attends flight school and learns fun aeronautical tidbits, which he in turn passes along to me, especially while flying low to the ground in single-engine aircraft (“See those blue lights in the distance? The runway lights? Watch this. I can turn them on and off with this button here.”). He’s 24 and from Kentucky, so his beverage tastes run mostly to bourbon and beer. Plus, he’s been hanging out with his fellow future pilots for the past two years, and after visiting him recently, I can tell you first hand: It’s quite the casual scene. “I could really go for a cold one,” he said, as our cab swung up to the glassy Trump. “Think they’ll have Fat Tire?”

“Um, maybe,” I replied, figuring evasion was my best tactic.

 It was Lee’s first time inside The Donald’s den of decadence, and he eyed the polished wood and gray velvet lobby furniture suspiciously as we walked toward the steps leading up to Rebar. “Bet this was cheap,” he mused. I led him into the bar with a flourish, watching to see if he, like me, would swoon over the sightlines. Instead, we both heard a squeal and turned to behold an infant in a high chair gurgling through cocktail hour with her parents. “Oh look,” I said, pleased to trot out my favorite line from Sweet Home Alabama: “They have a baby. In a bar!”

We spotted two friends and settled into a couch, taking our eyes off of the drink list long enough to pick pieces of sushi from passed trays. Round one: the Fall Blossom (a gin martini with cactus ginger and pear puree; $15) for me, and the Pump Jr. (pumpkin liqueur, Godiva White, and vanilla vodka; $18) for Lee. The Blossom proved sugary and bright fuchsia: fine by me. But Lee took one sip of the Pump Jr. and said, “Tastes like an Orange Julius.” We traded, because that’s what big sisters do. I would compare the Pump Jr. to trick-or-treating in a cup, perfect for dessert after dinner upstairs at Sixteen.

After a round of Yuza Limas (citrus puree mixed with sake and lemon vodka; $15), we switched to wine—there are only so many specialty drinks a person can ingest—and played guessing games about the other bar patrons (“Idaho or Omaha? Old Town or Wicker Park? Married or hot affair?”) until it was time to bid the view adieu. On the way out, Lee cleared his throat and tapped me on the shoulder. “That sushi was great, and I know the pumpkin cocktail was probably about 500 calories,” he said. “But would you say it totally filled you up? Because, you know, I was thinking we could order a pizza.”