Drunk in Love: That Time I Proposed to a Girl for Free Wine

I woke up drunk, which was pretty standard for a Friday morning in college. The night before was the annual Senior Semi-Formal; basically, it was an excuse to get dressed up like horny 18 year olds going to prom and binge-drink at a school-sponsored event somewhere in greater Ithaca. I don’t remember exactly where because, like I said, I was pretty drunk before my friends and I piled into the giant buses that transported us safely to the Semi-Formal.


My memory of that night is blurry at best, filled in by the exorbitant amount of pictures I took and has settled into an alcohol-soaked, teen TV show drama-like montage of shot-taking and grinding on the dance floor, all set to Journey’s “Don’t Stop Believin’,” which somehow saw a revival that year.

I was pretty drunk the next morning when, at 7am my alarm buzzed, alerting me that I had exactly an hour to get dressed, grab my roommate, meet our friends for breakfast at the dining hall, and grab our other friend, who was still too wasted to function in order to make the trolley that would take us to our Senior Week Wine Tour.

Binge-drinking was the theme that week. After all, we only had a few days left before we were college graduates and it was no longer appropriate to drink every night of the week, go to sleep in the middle of the night, wake up the next morning, eat free Belgian waffles from a dining hall, and continue drinking well-into the night.

The wine tour was scheduled to go to three different Finger Lakes wineries; I was exceptionally excited because, up until that point, I was pretty much a dedicated hard liquor drinker and had just gotten into wine, which I had decided was like a juice, but with a happy ending.


So, we got on the incredible San Francisco-inspired trolley and begin our journey around Cayuga Lake.


Oh, what a journey it was. Remember that friend I mentioned that was too wasted to function? Well, she ended up turning 50 shades of green and puking in a paper bag, effectively coining my oft-used phrase when someone asks me if I’m “doing well” after not feeling so hot: “It’s ok, I threw up in a bag.”

After that, though, she was champion, and by the third winery, she was toasting with the rest of us.

On the way back to campus — and, I’m not 100% sure on the chain of events here, but I digress — The Powers That Be decided that we had the time to make an unscheduled visit to a fourth winery, Hazlitt Vineyard, home of the Red Cat wine.


More wine = AWESOME. Plus, who could resist a wine label that had it’s own song:

Red cat, red cat

It’s an aphrodisiac

Red cat, red cat

It’ll get you in the sack!

At that point, I was blissfully drunk, and with only one winery left with enough tastings to amount to only one more glass of wine, I knew something needed to be done to someone acquire more wine and extend the tasting.

“What can we do to get more free wine?” I asked my friend, let’s call her “Vivianna.”

“Seriously,” she responded with conviction. At this point, her cheeks were a rosy shade of pink.

“Oh my god, I should totally propose to you!” I exclaimed.

“Absolutely! Yes! That is amazing!”

We filled in our other two friends on the game plan:

“We need a crier. Someone, a good friend to be so happy and overjoyed by the news that she would be overcome with emotion. [Let’s call her] Kayley, can you do that?”

“I’m on it!” Kayley shouted.

“We need to make this authentic,” I said.

“How are we going to do that?” Vivianna asked.

“Do you have a ring?”

She raised her hand and showed me a ring that her boyfriend-at-the-time had given her.

“That’s perfect!” I said as she placed the ring in my hand. I slid it into my pocket. “We have to be serious about this, though.”

“You have to walk in holding hands,” Friend Who Threw Up in a Bag said.

“Yes,” I said, “We have to make it look like we’re totally in love.”

Vivianna’s face turned bright red and an inescapable smile spread across her face. “I can’t believe we’re going to do this. This is crazy.”

I had a feeling that, due to her inebriation, she didn’t think that I was actually going to go through with it. Little did she know that nothing comes between a man and his wine, especially when said wine is F-R-E-E.

The trolley drove up onto the gravel parking lot and, one by one we filed off the bus. As we stepped off, I grabbed Vivianna’s hand pulled her close to me. She instinctively took my arm and wrapped it around her shoulders. We looked like a young couple, [drunk] in love.

As we entered the winery, I kept going over the Big Proposal in my head: I needed to wait for the right moment, when everything was quiet and I could easily grant the attention of everyone in the winery with my Grand Romantic Gesture.

My heart pounded with each new wine we tasted, and as the session dwindled down, I knew it was either now or never.

I waited until the bartender poured us all fresh wine to taste. I didn’t tell Vivianna that this was the moment. I didn’t say anything to anyone. Instead, I slowly got off of my stool, grabbed her hand, and got down on one knee.

It didn’t take long before someone realized what was going on.

Notice the reactions from everyone in this picture. Genuine surprise.

Vivianna was actually caught off guard as I dove into the half-assed speech I had prepared in my head about how she was my best friend and that I couldn’t imagine my life without her in it. I spoke to her as if I was confessing my most intimate secrets to the love of my life: I told her that ‘graduation was upon us’ and that the ring was a symbol of my undying love.


“Will you marry me?” I asked.

Everything around me was a blur. Everyone from our trolley was staring at us. Two girls that we didn’t know that we next to us were crying. The group of older men and women at the wine bar behind us had turned around and were looking on with stars in their eyes, as if they had just witnessed a miracle.

Vivianna was bright red, flashing a toothy smile, and drunk grin that paired perfectly with the tears in her eyes.

“Yes!” She exclaimed.


At this point, Kayley was crying. Real tears.

The entire vineyard was clapping.

My Senior Week t-shirt was soaked with sweat and my forehead was glistening and I didn’t know if it was from nerves, the excitement of the proposal, or my wine-soaked drunken stupor.

Drunk selfies were a thing in 2008, too.


After we embraced, the bartender shouted, “FREE WINE FOR EVERYONE!”


Now, nearly eight years later, I’m a point where I look back at those moments and ask myself if I’m truly living life to the fullest every single day. Those were moments of carefree happiness, when I didn’t think about how tomorrow would effect today.

The years are ticking by like second hands on a clock and as seconds become minutes, minutes become hours, hours become days, and the days require much more than drinking wine and planning fake marriage proposals. At some point, in the days, weeks, and months after that day on the wine tour, I started to become an adult. Ideas like “student loans” that, up until that point were just faint whispers and abstract concepts became as real as the fears I had about how I was ever going to survive a life post-college. Somewhere, somehow, I became an adult with a big-boy job and an endless stream of bills that don’t pay themselves. I stopped planning fake marriage proposals and, over time, staying in contact with Vivianna and most of my college friends became more and more difficult, until it became clear that I would never again be the person I was back then.

But that’s OK. We all grow and change and move away and become the people we were meant to be.

At least we have the memories.

Memories are much more than stories to tell at cocktail parties or at reunions. They are forever a part of me, my soul, my history, and I love them.


Sometimes, they’re all we have.



  1. i’m crying over this. Tears of joy and tears of how much I miss you (and shh…but tears about how much better of a proposal this was than my “real” marriage proposal should have known then) … but I want you to know that your friendship means the world to me and I know we don’t talk often (at all) but I think about you all the time. I read your blogs and your FB status and smile at the man you have become. You have grown into your own and become someone I truly admire. I love you forever and I’ll always remember that day and always have a special place in my heart for you. ❤ Vivianna

    1. Awwww…thank you so much, #bleedinglover. You mean the world to me, and I miss you every single day. Seriously, not a week goes by that I don’t think about you and how you’re doing and miss the hell out of you. Also…our engagement, for however short it lasted, was thebomb.com!

      Love you “Vivianna”!

  2. This is such a great story! So well written and just so funny. What a wonderful way to get free wine. Its funny because every time i see a proposal at a restaurant or out in public, I’ve always wondered if they were real or not (I’m strange I know….or maybe just too pessimistic) because they always get a comped dessert or whatever. I think I might have to try this.

    Great piece!

    1. Aww thank you! Although I’m pretty sure most marriage proposals are real, it is funny to think about the stories behind them. When this happened, one of the girls who was on our trolley actually turned to us afterward and was like, “I just got engaged too! Isn’t it just wonderful!” Of course I had to fake that, too…I wonder if she ever found out it was a sham…

  3. THIS is such an awesome idea man! I could definitely pass off as a straight man and propose to one of my girls in a situation like this. You are my inspiration haha!!


Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s