Top 10 Failed Romantic Gestures (AKA The Myth of Perfect Movie Moments)

Most of us ladies have been there at one time or another. Wanting some semblance of our favorite romantic movie moments to come to us in real life. To be wooed. Swept off our feet. Enthralled by the thoughtfulness and passion and sincerity of our leading man. These moments come rarely, but we build up ridiculous hope and unrealistic expectation around that perfect kiss; that bouquet of flowers; that surprise birthday gift; that hand-written poem.

Let me tell you something. Perfect movie moments are more of a myth than anything else. They aren’t impossible, but they don’t roll out as they do on the big screen. Real people are complicated, complex, awkward, and just not that suave. So are relationships. Why? Read the part about real people two sentences ago.

You’re more likely to experience more failed romantic gestures than anything else. At least it seems I can recall more failed attempts than successful ones.

If you’ve been following along, you know that this is another post in my Dating Nice Guys series. So why is this a third installment? I hate to say it, but the failed romantic gestures I’ve had the pleasure of receiving have all been from the Nice Guys. And remember, when I’m talking Nice Guys, I’m talking that prototype.

Each time one of these attempts has been made – and you’re about to read about them  – I have desperately wanted them to work. However I come across, I am romantic and sentimental at heart. I want movie moments. Trust me. But as luck (with a twisted sense of humor and edge of poetic irony) would have it, these moments all fell flat when they occurred.

There I would be in the movie-moment and they always seemed forced, unnatural, unoriginal, or poorly timed. Poorly timed for any number of reasons. I’ve come to realize, even though I’ve thought I’ve wanted that scene from that movie in real life when it is recreated, it ends up pretty unoriginal and trite. Movies are magical. Real life, well, it’s often not a lot of the time. 

Do not misread me. Romantic partners exist and their attempts are not failed romantic gestures, not forced, not trite. Likely because their gestures are original and their delivery sexy.  Sexy = the confidence in knowing they’ve got a genuine idea (gift, plan, sentiment) and solid presentation of said genuine idea. And because it’s truly based off a deep knowledge of the other person and maybe even natural chemistry.

All that being said, here are my top 10 most failed romantic gestures, not in any chronological order or rank of failure.



The first time I met a guy from, he was lucky I met him at all. The day we had agreed we would meet, he kept me waiting around all day before he told me a time or we could solidify a place. I was going to tell him ‘forget it’ altogether but my family urged me to give him a chance. Maybe he was just nervous, they said. So, I did. I agreed to show up. When I arrived, I found him on a bench outside the restaurant, looking a little like Forrest Gump, and sitting with a brown paper bag in his lap. No, it wasn’t a box of chocolates. Though that would have slain me. (It also was not a gun or a bottle of liquor for those of you getting worried…)

I stepped out of the car and walked towards him. Before I was within arm’s reach he awkwardly shouted at me how beautiful I looked. When I got close enough, he thrust the brown paper bag into my hands. The bag was crumpled as so happens with brown bags that have been handled repeatedly. Then he told me he stopped at his favorite bakery on his way there, bought his favorite good to share with me, but then ended up eating some on the way there. What were those half-eaten baked goods in the brown paper bag? Chocolate covered Oreos. I’m not even sure if I ate them. He had been rooting around in that bag the whole way there and I didn’t know where his hands had been.

Points awarded for finally showing up, the compliment, and the thought to buy a gift.

Points deducted for holding me up all day, awkwardness, paper bags, and having eaten half of the gift on the way.


Then there was a time a guy I was trying really hard to like showed up at my apartment around Christmas to give me a Mickey ornament he had specially bought for me because he knew I loved that mouse. But then he ruined it by telling me he flew down to Disney on the family’s private jet- there and back in the same day. I wasn’t even sure I believed him.

Points awarded for remembering the one time I said I loved Mickey Mouse and knowing I loved Christmas and going out of his way to buy me something when there was no official relationship status to suggest we should be swapping gifts.

Points deducted for bragging about the private jet and how he procured the Christmas ornament.



I made out with a guy one night – we were in our 20s. Just one time. He had always intrigued me. Every time we were in the same place, I found him fascinating to talk with. He had a deep mind for a guy his age. He could talk about a variety of things which I found refreshing. The make-out sucked. He was a terrible kisser. When I turned down any advances for further physical contact, I thought that would be the sign to him. We parted ways and I thought that would be that. The next day I woke up with a fat lip.

Then, suddenly he was around all the time. One morning, I woke to a giant piece of sketch paper under my door with a Shakespearean Sonnet written on it with charcoal. Problem was, I didn’t know it was written in charcoal. So I read it, tossed it aside, and headed to the cafeteria for breakfast. When I got there a friend asked me what I had on my face. I had no idea that I had smeared charcoal all over my forehead. I looked like I fell face first into a flower bed on my way there.

Points awarded for Shakespeare, I guess.

Points deducted for giving me a fat lip, not getting the clue that it wasn’t that serious, showing up all the time, and writing the sonnets in charcoal.


In grad school, I started seeing a guy I met at Blockbuster. He quoted the Hangover and we bonded over the Tiger Song. He was nice enough. My friend gave him my number without my permission. She urged me to give him a chance. Go on a couple dates. Have some fun. He was a complete stranger to both of us which made me uneasy, so I spent a lot of time talking with him on the phone first. When I finally agreed he could take me out, he told me to dress up. That was kind of exciting, I’ll admit. I bought a great new blue dress and new jewelry and hoped for the best.

He surprised me with tickets to Oklahoma after an expensive dinner. Double points for good food followed by tickets to one of my favorite musicals. But then after Oklahoma, we took a spontaneous and somewhat creepy turn into an abandoned parking lot. It was winter, so it was extra cold and already dark. The soundtrack was blasting which could have meant complete innocence of a moment he was trying to manufacture or that he was going to use it to drown out the sound of my screams. It was hard to know and I held my breath.

Once we parked, he pulled me out of the car to dance under the light of a street lamp to People Will Say We Are in Love. This was our first date. It was a bit premature in the sentiment. He sang the entire song to me while making direct eye contact. Ever had direct eye contact for more than three minutes on a first date? It’s a lot.

Points awarded for the dinner and show tickets.

Points deducted for freaking me the fuck out and taking the Oklahoma thing a little too far.



The year my sister got married, we threw her a surprise bridal shower the same weekend as my birthday. I flew home. When I got to my parents that night, a bouquet of flowers and a package were there waiting for me. Both were from my new (new as in just a few weeks) boyfriend. I had never given him my address but he knew the town I grew up in. He called a local florist who was willing – to my horror – to give this totally random person from out of state my parents address so he could send me flowers. He used the same address to then rush the package. The package had a mixed CD.

After an absurd amount of love songs, his voice came on as the final track. He went on and on for a long while about how we were born to be with the other. Like truly, “you complete me.” To make it worse, because I hadn’t expected the last track to be a monologue of undying love, I was listening to the CD with my parents and they heard the whole thing. My mom told me it was sweet. And my Dad, well, he was laughing so hard he was wheezing. The message ended with him telling me he had something extra special planned for me when I returned. I seriously considered never going back.

Points awarded for remembering it was my birthday and trying to do something special.

Points deducted for snatching my home address from the local florist, professing we were meant to be, and not giving me a heads up that I should listen to the last track by myself.



I dated a guy in high school where most of our relationship was long distance. There was an immense amount of effort required to write letters as neither of us had immediate access to email at that time. This pre-dated most homes having computers and internet access. One time in the mail within a letter came a print out of our future baby’s name. I was not pregnant. We had never discussed children in any detail, certainly not to have named them.

Points awarded for….? Yeah … no points awarded.

Points deducted for assuming the existence and naming our future hypothetical child.



Same boyfriend as number 6. One time, over the phone, he slipped into the conversation that he had gotten a tattoo. I asked him what of. He told me my name. I laughed. “What is it really?” I urged. He repeated himself. I refused to believe him and eventually we hung up. Then a picture arrived in the mail. There was my name. Right between the shoulder blades.

Points awarded for believing in our love so much you took a needle to your back. I mean, I’m not even sure if that should be awarded but I’m certain that it hurt, so for your pain, you can have a few points.

Points deducted for taking a needle to your back! And etching my name onto your body! What. Were. You. Thinking?!



In undergrad, I had tried repeatedly to break up with this guy. To no avail, he wouldn’t let go. When I came back from a Christmas break, he was adamant that I spend the weekend with him so he could make it (the entire miserable semester together) up to me.  He planned a weekend of activities (most of which I had no interest in) and then hand wrote the “schedule,” filled with typos, onto some printer paper.  The schedule sat on top of a turned over cardboard box that was make shifting as a table. A teddy bear sat nearby with a heart in between its hands that said: “love me.”

Points awarded for attempting to apologize, trying to be thoughtful in preparing a weekend of activities, and spending the money on the teddy bear.

Points deducted for too little too late and typos.


First date. Ice cream at Friendly’s. They’ve got one of those machines with the claw and the stuffed animals. This date asked me for quarters so he could try to win me a bear. I politely told him it was thoughtful but I didn’t want one.  So then he asked the cashier to break a $20. I again told him I wasn’t interested in a bear and to not waste the quarters. He didn’t listen. He took the quarters from the cashier and the rest of his change and spent $2 trying to win a chinsy carnival toy I didn’t want.

Points awarded for persistence.

Points deducted for not listening.



Lastly, one guy wrote me a poem where I was metaphorically identified as a sparrow with a broken wing and he was the flower that protected me until I healed and then urged me to fly.

Points awarded for creative writing.

Points deducted for describing me broken as a result of personal shit I shared with him and then assuming the role and responsibility of ‘hero.’


Some of you are probably like, “You’re such a bitch.” How could you take all of these well-intentioned romantic gestures and just throw them out there onto the internet. These guys obviously adored you. That is true. They did adore me. These attempts were well-intentioned.  And if you were paying attention, I gave them credit where credit was due. But for me, they were all failed romantic gestures as evident by the points deducted sections of each instance above.

I’ve let go of the idea of those perfect movie moments. I still want romance and my socks knocked off, but I’m not looking for it in grandiose ways necessarily. Nor in ways that seem like replicas of a rom-com.

What I’m looking for includes:

A funny card when I’m having a bad day. A photo I love being framed and left for me where I’ll find it. The unexpected gift certificate to go get a massage because they know I’ve been stressed or simply just because they think I deserve it. Sharing a meme or quote with a romantic sentiment without prompting. Surprise! We’re going to stay at a hotel for the night: pack your bag. Showing up with something they knew I needed without my having ever asked for them to buy. The invitation for them to make me dinner; all I have to do is show up. Certainly, I would also welcome the unexpected gift – that pair of earrings, that journal, that book I mentioned nonchalantly liking in the store that one time.

Most importantly, I am looking for the encouragement to be me, to not keep myself small. To be told I’m adored as I am.

And the utterance of anything such as you’re my favorite writer or you amuse me or I love being around you. These for me are the things that resonate and make the deepest impacts. These are the real-life moments that can be magic. They are simple and thoughtful and show I have been heard and seen for me, as me, in real-time. Not based off what they think they need to do or what they think I’ll want because they saw it on TV, read it in a book, did it for everyone before and it always worked, or because they are trying to keep me attached to them.

The romantic gestures that I want are the ones that prove my partner is paying attention and wants to do something for me that doesn’t serve them at all. That isn’t showy. That isn’t begging for wild applause.




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