“You're a lot prettier when you don't talk.” -- A grumpy and pretentious executive speaking to my friend Holly after he scratched his Rolex during dinner.

"Thanks for coming out with me tonight. You see, I really don't get out much, so I really appreciate you getting me out of the house.” -- Holly on another date at a West Loop bar with a man over 30, who failed to disclose that he also lives with mom.

“I've never gotten my shirt taken off by an Asian before. (Silence). Maybe you could do that.” -- An overconfident MBA student at Manor nightclub in River North.

“With you, I don't think I'd need any date-rape drugs”. -- Following a romantic dinner at Mia Francesca in Lakeview.

“I'm not looking at your boobs! I don't ever look at boobs when they are wearing clothes!” -- On a Cubs game date with an endearing meat head.

“What?! Is it because I'm White?!” -- A drunk and possibly frustrated suitor approaching a group of Asian women at McFaddens in Gold Coast.

“My woman loves me. And I don't know why.” -- A drunken Rusty talking about Suitress No. 4, commonly referred to as just No. 4, at Merkle's bar in Wrigleyville.

“Aww man, I look so creepy. Now I look creepy. Can you please walk in front of me?” -- After a failed attempt to approach a woman, Rusty realized he was walking right behind her in the heavy stairway of Burton Place in Old Town, using me as a physical barrier to the alleged creepiness.

“Oh sorry honey, but you are just the cutest thing. You're beautiful! Come here!” -- The friendliest gay man at Hamburger Mary's in Andersonville who accidentally elbowed a woman dancing with friends, and then offered her a hug.

“They were cheap. Plus I missed so many of your birthdays, I wanted to make up for it.” -- A long-lost crush explaining why he sent birthday flowers. First, in true dense-male form, and then second, quite romantically.