The One with Flirting

“Soo… uh… do you like…cheese?”

Its my favorite quotable line from She’s the Man as Amanda Bynes is teaching Channing Tatum how to flirt with his dream bae. I have never related more to a character in that moment.

Its funny because I feel like talking about cheese would probably be a step up for me in how my flirtation goes. I recently told a friend I had been flirty with a guy and her response was “the kind where the guy actually picks up on it or your usual style?” And she wasn’t wrong. Subtle humor/flirting would be putting it lightly.

In highschool my friends took pity on me because it was truly pitiful and one day decided to try to teach me to flirt. Honestly I don’t even remember what was said but whatever it was obviously didn’t stick. When your flirting style is being in the same room or saying something nerdy I feel like rom-coms have officially failed me. Probably because I wasn’t a fan to start off with.

But beyond being bad at flirting, I am also terrible at responding to flirting. Like SO bad. One of my favorite memories now was my most painfully embarassing one for years. When I was in college I worked at a coffee shop for awhile and every now and then we would get guys that came in through the drive thru or in the store who were a little flirty. In true to self fashion, I’d find a way to be busy and away from them because I honestly didn’t know what to do


Well one sunny day I was sitting against the drive thru window on a slow day just chatting with my coworkers when one of them mentioned that someone was coming up to the window. I turn around to see a cowboy- boots, hat, freckles and all- striding toward the window with a goofy grin on his face.

Hey! “Um yah can I get some coffee frappuchino?” Yah sure but you’ve gotta come inside, we can’t serve pedestrians in the drive through. “Um hold on I’ve just got some questions for you” Sure if you come on in we would be happy to answer your questions.

At which point I frantically close the drive thru window and run away only to the howls of the girls I work with about “oooohh he likes you! He’s gonna ask for you number!”

I proceeded to spend the rest of the bit hiding as they kept an eye out and saw this kid walk in and look over at the coffee shop and he and his buddies went over to the video section of the book store. He never came over so I honestly thought I was good. Then about 15 minutes later the drive thru beeps and I put on my friendliest, afternoon texan coffee shop voice and asked them how I can help them.

“I’d like a large coffee frappuchino.. and your phone number”, I hear amidst snickers and what I can only imagine are elbows from his buddies egging him on.

What size frappuchino would you like? I say, pretending its not happening meanwhile I’m trying to get someone else to take over the order because I CANNOT handle this. I am MORTIFIED. He finally pulls up to the window after shameless flirting that I bumbled through and stuttered past.

While I am trying to take his money to get him out of there as quick as possible he is- at the behest of my coworkers- asking me what time I get off work. I try to avoid the question and mumble something about “oh I don’t know it depends sometimes, kinda, ya know…hard to tell” before one of my antagonistic coworkers yells out “SHE IS OFF AT 6!”

This prompts Cowboy Bud (yes that was his actual name) to then ask me if I like movies. Guys, at this point in my life I had gone on like 3 dates total and half of those didn’t even count as real dates. So while at 29 I might be a pro at dodging questions or turning someone down (spoiler alert: still not), I definitely was not at 20. So each painful questioned he asked I answered.

“So do you like movies?”
Um yah…I do
“Do you have plans tonight?”
(Oh for the love of God think of something) Um no…
“How about you meet me at the movies at 7:30 tonight?”
Um ok…

Guys I can’t tell you how red my face was or how many times I stuttered in the conversation or said something stupid that I don’t even remember now almost a decade later.

But what I do distinctly remember is after Cowboy Bud drove away and my coworkers were hooting and hollering and making all the kissy faces telling me I now had a boyfriend… After all that, I remember is he and his buddies driving back through the drive thru and him through the drive thru intercom asking me how old I was…

Warning flag #1 was his name was bud
Warning flag #2 is that he asked me out through a drive thru window
Warning flag #3 is that he asked me how old I was

“I’m 21.”

I literally had to take off my headset because it got super loud as his buddies laughed and OOOOO’d at my revelation.

“Why? How old are you?”

“I’m sixteen” he said, howling with laughter before he peeled out of the drive thru with an exclamation of seeing me at 7:30.

Guys I was absolutely mortified.

Not only had my most epic disaster of flirting/dating engagement been showcased, but it had been showcased to a 16 year old boy who had had success in getting me to agree to a date out of sheer panic.

At 21 I was barely starting to figure out how to put on makeup and how to be confident in myself. The fellas had not been beating down the door with date invitations so I honestly didn’t know what to do at this point. I knew that I didn’t want to go on a date with him even before I said yes, but I espcecially knew I didn’t want to go out with this jail bait.

Guys, I seriously cringe to thing about just how uncomfortable I was. I remember returning to the dorm that afternoon and urgently calling my most boy savvy friends to help walk me through what to do next. I knew that ghosting him (before that was even a word) was not in my character so I knew I had to show up and not leave the kid just hanging.

I’ve learned in recent months, ok geez maybe weeks…. that I have a difficult time relaying my feelings. It’s not that I don’t have valid reasons. Vulnerability is hard, uncomfortable and well, vulnerable. Maybe for you the most uncomfortable moments to share your feelings or thoughts are in moments of conflict. Maybe thats where vulnerability feels most risky. I certainly get that.

For me, dating brings up my most vulnerable moments. The powerful sting of rejection sits so close to the surface and is daunting. In the years when I was active in online dating I stopped counting the number of times I’d been stood up when it hit dozens.

Yes. I said I have been stood up dozens of times.

I think the sting of rejection is enough and even in my naive years at 21 I still knew that rejection is tough enough but standing someone up to avoid my fear and discomfort wasn’t fair and was cowardly. Not to say I have stuck to that every moment of my dating life but I try.

So my friends and I came up with and literally rehearsed what I was going to say to this guy when we got to the movie theatre. I needed a lot of help haha.

So as we pulled up to the movie theatre and I see this 16 year old cowboy standing there with his cowboy boots, fat buckle and clearly nervous demeanor. I tentatively but surely walk up to him and blurt out the fastest, most blurred together 10 second sentence rejection in the quickest, rip-the-bandaid-off way I knew how.


I feel like what I said had to have been more suave than that but knowing me then and now I know that it absolutely was not. His response was to this day one of my all time favorite responses in my “dating life” when he said

F*** this. I’m drunk anyway

And sits down on the curb where he waits to have his mom come pick him up.

I wish I could say thats the only time I waited for a date’s mom to pick him up in my adult life. More stories for another day. But as I ran-walked into the theatre I experienced a couple of things in a rush. Instant relief- oh my God, I’m so glad I do not have to go on a date with this guy. Shame/embarassment- I cannot believe I was so dumb and inexperienced in navigating flirting that I said yes to a date with a 16 year old boy! And nausea. Yep, still to this day, vulnerability makes me nauseous. I mean my therapist says thats a good thing and I should take it as a sign that I’m doing good things when I get nauseated. But what do therapists know (I say as a therapist in training).

For so many years, this story was the one that was my most embarrassing one. By a long shot. I felt so embarrassed by my lack of skills, calm, and ability to navigate that without someone hand-holding me through it. But then came the online dating years when I navigated a lot of awkward, embarrassing dating moments. And you know what I learned?

I am resilient

I am still so thankful for the awkward dating stories I’ve lived through and the terrible conversations. I’m grateful for the times I’ve shot my shot and been shot down. I’m (mostly) grateful for my nauseaous moments when I shared vulnerably how I felt in moments of conflict or in moments of great joy and affection. Because in all of those things, I learned that I can. That none of those awkward, terrible, embarassing, or painful moments were the end of me. In fact, I walked away wiser, kinder, and with new abilities. To navigate conversations with awkward people, to be genuinely curious and express interest in people I hardly know, to enjoy my favorite foods and coffee (sincerely) when I’m stood up, and to ultimately be unafraid.

I still have my moments when I come across something new in life, love, faith that makes me nervous but looking back on the moments I’ve already lived through successfully makes me realize that the “worst” that can happen ain’t got nothin on me.

I’ve watched so many people around me who approach dating in such a timid way, terrified to date or be vulnerable for fear of rejection. So many guys that I’ve heard share their fear of expressing interest or asking a girl out for fear of rejection. So many girls who fear that their vulnerability will scare away the very ones that they treasure.

I had a wise friend once tell me, “If the guy can’t even ask you out, he’s definitely not ready. It only gets harder and more vulnerable from there. It’s so much harder when you have to tell her you love her. When you have to ask her to marry you. When you have to raise kids together.”

Here’s the thing. You might not be successful the first time. You might not get what you are hoping for in that moment. But you will grow and become the person who is successful and who is able to get the things in relationship that they are hoping and praying for. But it requires taking a risk. Try. Fail. Be embarrassed. Learn. Do it again. Find out how resilient you are. I think you will be quite surprised.

I still haven’t mastered the art of flirting. And I’m still learning how to share my feelings with someone in vulnerability. But the embarassing stories have become part of the adventure.

So I dare you! Be brave. Master your embarrassing stories. Find your resilience.

I am taking part in the Sacramento Youth Center ‘s embarrassing story challenge for #givingtuesday Lets spend the weekend laughing at some funny stories. #sycgives

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