Dear Ryan and Sarah: Double Dutching in Cleveland

Hi Ryan and Sarah,

Great job with the blog; your posts are pretty hysterical. Question for you guys, I was at the bar with a friend on a week day when a cute girl across the bar caught my eye. She was sitting with another girl and a guy who was clearly hitting on her friend. I ended up making up an excuse to not go over to talk to the cute girl, but it was really because she was sitting at the bar in conversation with her friends and it was a week day so I figured she wasn’t looking to talk to anyone.  I also didn’t have a willing wingman with me to help me break the ice. Did I wimp out? Any advice for me next time?

Sincerely, Double Dutching in Cleveland

Thanks for writing in Double Dutch, it seems like you definitely wimped out but it’s okay. Tomorrow is another day and you can hit on girls then! My best advice here would to say just let things happen as they do, don’t consider any one night to be more “appropriate” to hit on girls than the next. If you end up meeting someone cool on a Wednesday go and talk to her! You will probably have a better conversation since the two of you won’t be as drunk as you will be on the weekend. You might actually be able to have an intelligent conversation with her.  If it doesn’t work out, it doesn’t work out. You’ll never go home after a couple casual beers and complain about how that girl was “the one that got away.” It’s a Tuesday!! On the other hand, you could take a day that is usually just for lounging around and meet a cool person. There are always less people out during the week so you might get lucky when there is no competition and meet a cool girl.  Furthermore, wing-men or wing-women are only there to help you out so you shouldn’t use them as a crutch. The girl would be able to see that you are a confident individual if you could have gone up by yourself and talked to her, regardless of whether your friend chipped in or not. So take my advice, get out there again with your bros and meet some new people!


Whaddup Double Deeeeeeeeee – thanks for reading and writing in!  It makes me feel so cool to have a reader in Cleveland (never been there, but sounds awesome).  Wait so is this a thing now?? Not hitting on girls on a weekday??  You crazy, boy!  In my opinion attractive girls are a dime a dozen… they’re literally EVERYWHERE.  Who cares that you didn’t talk to an attractive girl at the bar?  They’ll be one there tomorrow, I promise.  Now.. if you actually have feelings tied and felt a bit of a spark and/or thought of something beyond just a hookup (call me naive but I still think this is possible… even after being friends with Ryan), then I’d say… what do you need a wingman for?!?! You’re interested.  Go get her.  I may write a separate post on this altogether, but as an extremely independent, strong-willed, stubborn, mildly successful, seemingly attractive female… I will say that if a guy doesn’t have enough cahonas to approach me, then he’s not the guy for me.  I have a tendency to wear pants in relationships and I don’t want them!  So if you’re genuinely interested in a girl, man up and take the initiative to talk to her; separating the men from the boys right there!  If you’re just looking for a hookup.. meh.. it’s not really my thing, go to Ryan for that one 😉 Wishing you the best of luck with the ladies – look forward to hearing from you again!


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