Flirting in the Age of Masks

Let me begin by saying that I am happily married and that I have no intention of going out and flirting with anyone, let alone my wife (don’t worry, she’ll never read this...I think). That being said, as I walked through Target on my way to purchase a new staple in my diet, garlic hummus, I ruminated on how I would go about flirting with an attractive woman I might potentially run into, because everyone knows the supermarket is as likely a pickup joint as a bar at my age. My first thought was to hide the garlic hummus and my second thought was; I don’t know how to flirt under the best of circumstances. I’m lucky I’m married as it is, but I digress.


This started out as a thought experiment while I was shopping, and since this is really the only time I get out of the house these days, I took my time and really thought about it. After many hours of wandering aimlessly around Target, I came up with the only tool I could think of in my flirting toolbox: smiling. As I thought about it, I smiled and a sweet old lady walked by and I directed my smile at her. She ignored me! How rude! Then I realized, I have a mask on and all she could see were the serious wrinkles I have around my eyes and she probably thought I was either glaring hatefully at her or I had gas, so no wonder she ignored me. I stood there, cradling my garlic hummus wondering, “If this wasn’t a sweet old lady (who wasn’t wearing a mask, by the way…tsk...tsk) and instead, a MILF, how would I flirt with her?”

I’ve read enough Men’s Health magazine articles in my life to work this out, so let me give all you men out there some advice about how to flirt in the age of masks. My first advice is to not refer to any woman as a MILF. That only works in movies and you are more likely to get slapped and have a #metoo thrown in your face, and deservedly so. Second, you have to be dressed the part. I live in Florida and flip flops are my go to footwear. While I haven’t started to wear socks with them, they don’t exactly scream, “I’m hot and available” and instead scream, “clip your damn toenails.” So if you are in the market, make sure you wear clean clothes, a nice pair of shoes or sneakers (something like Sketchers, not your scuffed up running shoes) and comb your hair. Of course, in the age of Corona Virus, a nice haircut isn’t always easy to come by, so do what I did, shave it off. Face it, your hair is already thinning and your comb over isn’t fooling anyone and you are too old to wear a baseball hat. No woman is going to look at you if you look like Alfalfa or an aging rock star (unless you are actually an aging rock star, then stay out of my Target, you've had enough fun already!)

Tip: Stay away from any women shopping for any phallic type produce (eggplants, cucumbers, etc.) lest you want to start off with an unflattering comparison or you are really witty and can make it work.

Ok, you are dressed decently, your hair is properly coiffed/shaved, and you are loitering around the produce aisle which is where you can expect to find the attractive women (though I think I'd have better success hanging around the snack aisle). What now? You amble over, make eye contact and smile…and she ignores you and walks away very quickly because you are creeping her out. Of course she did, because you were just staring at her and she couldn’t see your smile. This calls for some ingenuity!

Ok, now you are all set…you have the hair, the shoes, the clothes, you’re avoiding intimidating cucumbers and you have your smiley face mask on. Now it is time to engage your smoldering eyes to convey that you are smiling, specifically, at her (work on this in the mirror, because my first 50 attempts ranged from conveying I was severely constipated to I am going to kill you and cut you up into little pieces a ‘la Dexter). How do you know it worked? I don’t know, I’ve been married for almost 15 years, but I say, if she doesn’t run away screaming, you got your point across so take a chance and just go say hello.


There you have it, the worst dating advice you've ever received, aside from that time your mom told you how much girls liked boys who joined the school marching band. Thanks Mom.


Comment below on how you are handling flirting today in the Age of the Mask, and help your fellow masked brothers out.

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