Sweatpants Guy Meets Ponytail Girl

If you’re between 25 and 45 and single or know someone who is, then you’re probably familiar with online dating.  The Internet makes it easy for singletons to find people who, on paper, are a perfect match.  We seek our mates online because as we say to each other “How else will we meet someone?”  Yes, we’re all walking around out there but unless we log on to one of our many interweb gadgets, we’ll simply never meet.

I’ve had many experiences with online dating.  Some good, some bad and some downright hilarious (fodder for a future blog post perhaps) but the problem I continue to run into is authenticity.

Let me explain. For those of you who aren’t familiar with online dating, here is a download:

You log on to your favorite dating site, find someone attractive, and then you chat via email and instant message with chosen attractive person (sometimes for a very long time). In these emails and IMs you flirt. You use your best vocabulary, you talk about all the smart things you’re both into and how clever, yet grounded and normal you both are and then, finally, someone bites the bullet and types, “let’s meet”.

You meet somewhere not too romantic but not too casual and then the interview begins:  “What do you do?”  “Wow, what an interesting name you have.”  “I’ll order wine if you do” and so on.   At the end of all of this conversation you walk away feeling it went fine and then four out of five times you never talk, email or IM that person again.  I think it’s because even though you were both respectful and somewhat interesting you don’t really “see” the other person. You know a whole lot about how much he loves NPR and running marathons but you have no idea how he treats old ladies in grocery stores or how he looks in his sweatpants on a Sunday.  But we have to online date right?  After all, how else will we meet someone?


I was in Whole Foods a few weeks ago when I noticed this guy in the checkout line next to me.  He was smiling and chatting with an older lady behind him and helping the lady in front of him pick out some sort of chocolate bar.  He was charming, funny and helpful and he had these ladies beaming.  Actually, he had quite a few shoppers beaming.  Folks would pass the line and smile or make a remark about a conversation they had with him earlier in the produce section.  It seemed like he affected the whole store with his dynamic personality.

Sweatpants Guy wasn’t overly attractive and per my colorful nickname, he was wearing an old tattered sweatshirt and yes, sweatpants. Normally a guy in sweatpants at the grocery store would be a red flag but not this guy.  He seemed like a lot of fun.  He was happy and true.

As I left the store I seriously thought about saying something to him. I wanted to say, something about how his personality was contagious or how I thought it was nice the way he treated the older lady in the check out line. Instead, I just walked out of Whole Foods and into the store across the street. While waiting in the check out line at the second store, I saw Sweatpants Guy again.  He was heading up the aisle next to my check out section. I thought, ‘okay this time I’m going to say something to him, this time I’m actually going to communicate.’  I was about to reach over and tap him on the shoulder when a super cute girl wearing a long, straight ponytail approached him.  She was extremely nervous and her voice shook just a little when she said “I never do this, I swear, but I think you’re amazing and you seem like so much fun and, well…here’s my number.”  I stretched my neck to see what she had in her hand and it was a yellow Post-it note.  She had written her number on real paper!

We waited, the ponytail girl and me. We waited to see how Sweatpants Guy would respond to the numbers on the Post-it.

He looked her straight in the eye, gave her the most authentic and lovely smile and said, “You just made my day. Thank you so much, wow.”  She giggled a laugh much younger then her years and repeated what she had said before. She told him he seemed like a nice guy and to have a good day.  Then she half skipped out the door.

As fate would have it Sweatpants Guy and I left the second store at the same time so this time I turned to him and said “It’s not every day a gal asks you out in the super market.”  He flashed that amazing smile and said, “I know, she really made my day.”

I have no idea if Sweatpants Guy and Ponytail Girl got together but I love that I was there to witness their real life encounter.  As I walked home with arms full of groceries I decided to make it a goal to ask a complete stranger out on date in person before the end of the year.

Thanks Sweatpants Guy and Ponytail girl for reminding me there are other ways to connect, ways that are spontaneous, true, real and a bit magical.

Have you ever asked a total stranger out in person (in the last 5 years)?  How did it go?


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