matchmaker’s secrets for singles of sparking conversation

Chicago has tons of great bars, events, and venues to pick up sexy singles like you, but it’s often difficult to mingle smoothly and say just the right thing. Mingle Around has compiled the best tricks to ensure a date with first impression conversation.

let’s start with the basics

Eye contact and a genuine smile will immediately show interest. Beware the creeper smile and staring too long, though! Also, if you look around too much, you may come off shifty or looking for the next best thing. Give her/him all your attention in a friendly way.


compliment

It’s a simple trick, but everyone likes to hear how great he or she looks that night! A great dress, tie, or watch is an easy conversation piece and nothing out of the ordinary to approach someone about. Keep that genuine smile in tact, and you’ll get to know this good-looking bar partner with ease.


mutual people watching

Everyone knows they’re looking at the 40-something man with the awful toupee. If you catch him/her staring too, the two of you can giggle over the silly people watching at the bar. You may be able to bond over critiquing people’s outfits or the bartender’s cheesy flirting techniques with the ladies. It’ll give you a sense of their humor and a feel for their personality. However, watch out for seeming condescending or judgmental. Keep the banter light and the conversation as positive as you can overall. Rude comments are so not attractive!


use a cheesy pick-up line, with major sarcasm on the side

Sure, women hate them, and they’re hardly used on men, but if you make it a joke, you’re sure to get her/him to crack a smile! Chalk up the cheesiness because delivery is everything here. And, don’t be afraid to make fun of yourself a little bit. If he or she does reject you, at least you can laugh it off. Here are some classics:

  • 1.    Shall we talk or continue to keep flirting from a distance?
  • 2.    Excuse me; I just noticed you noticing me, and I wanted to give you a notice that I noticed you too.
  • 3.    Aren’t you the guy who is supposed to buy me a drink? (How could a true gentleman say no?!)

It’s a long shot, but as long as you are your most confident self, it’ll surely break the ice.


It’s definitely nerve-racking to talk to a good-looking stranger, but with the right event, mood, and killer confidence, who knows who you’ll meet. You’d regret returning home from a night out not meeting anyone new, so a little innocent banter won’t hurt!


Where do you want to try out these tricks? Mingle Around has plenty of upcoming events for you to check out!

 
 
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