Category: Flirting

Celebrate Your Birthday At the Chicago Cubs Game to Get a Date

America’s birthday is always a fun day to get out and meet people who are taking a moment to celebrate all that we have and all that is possible. You can make your birthday special too. In addition to all of the free things you could acquire popping around to chain restaurants … free Grand Slam at... Read more »

Chicago's Top 10 4th of July Events For Singles

Fireworks. Blech. Not a fan. But they bring people together, especially for the 4th of July holiday, so sometimes I get on board to watch them. I mean, if it could end in me getting a date, I would usually do it.  Other times, I don’t want to be anywhere near them. We all have... Read more »

A Horrifying Message on Tinder; Or Maybe It Was a Compliment

“Hope it doesn’t completely horrify you.” My first instinct was that if you need to follow up a message with a sentence like that, it might be best not to send it in the first place. Then, I thought, maybe it was meant as a compliment, which some of my friends agreed with that idea.... Read more »
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Crafting A Great Opening Line Doesn't Always Take A Lot Of Time

My older (by two years) friend told me that when you turn 40, everything changes with online dating because the cutoff date that most guys use is 39.  Your choices dramatically change.  So as I’m less than 40 days away from my 40th birthday, I jumped back on Match.com a few weeks ago to test... Read more »

Even Though I Won't Be Dating His Friends, They Factor Into The Dating Equation

“Don’t leave!” the random guys pleaded as we walked by. “Sit with us.” “I’ll get you a chair, lovely lady,” one guy said to my friend. “Oh, I can get one for you too,” he said when he finally noticed me. This is what happens when you go the bar with a tall blonde.  But... Read more »

Gavin DeGraw Inspires My Top 5 Flirtable Concert List

I’ve seen the New Kids on the Block in concert many times, both when I was a teenager and a few more times in my 30s.  That’s not why I’m single.  Well, at least I don’t think that’s why I’m single. But it is why I haven’t met anyone at these concerts.  Even when they... Read more »
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How Are You Single With A Rack Like That?

If only it was that easy.  To like someone based on just one thing.  Nothing else matters.  Nothing gets on your nerves.  You’re focused on what grabbed your attention in the first place.  And you never lose that focus. I was at a wedding over the weekend when my friend made the rack comment, or... Read more »

The Chicago Blackhawks Make The Best Wingmen

I’m not the biggest hockey fan, but I’m always excited when the Chicago Blackhawks make it into the playoffs.  The whole city rallies around them, which means the bars are filled with fans no matter what night of the week the games is played.  And most of those fans are guys.  In fact, when I... Read more »

Week 12: It's Not A Lie If You're Giving Out Free Beer During March Madness

Free beer gets dates.  It just does.  And March Madness makes it that much easier.  Guys have been doing this for years.  Buying girls drinks in hopes of getting some time to talk to them, and with that time hoping to convince them that they should go out.  Or hook up.  It’s a fine line.... Read more »
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I Should Probably Feel Guilty For Running Experiments On Men, But I Don't

I’m guilty of enjoying the dating experiments I run whenever I’m out.  Whether it’s at a bar or at the airport, just about every interaction I have with a stranger is because of the happy feeling I get when I can analyze a situation.  This shouldn’t be a surprise to those of you who read... Read more »