My Big Fat Italian Engagement
Where do I begin to tell this story? If you’ve followed along for the past four years, you knew my dating life was more like a disaster story than anything. Somewhere along the quest of finding what I truly wanted out of life, I finally failed enough to prove myself worthy of the relationship of my dreams. And you know what? It’s a hell of a lot different than you’d think. The funny thing about finally getting what you want is that you probably won’t get it until you’ve become completely unattached from the outcome. At least that’s how it worked out for me.
Rewind to about two years ago, a was still single and had enough dating fails under my belt to make me feel completely exhausted by the modern dating world. Dating exhaustion is real and it ironically can mimic your daily life if you by chance happen to work in sales. If you’ve ever been a sales rep like me, you probably started out with a bit of an ego. You know your product, you’re good at your job, you show up and you’re ready to slay the day until a prospective client tells you no. Sales rejection, just like any rejection, can feel like a kick to the ego. Whether you’re familiar with the dating rejection or sales rejection, the first few no’s that you get can send the average person into a tail spin. On the flip side, once you get some momentum going, you start to brush off the no’s. By the end of my sales career, I was so thankful to receive a “no” from prospective clients because that meant I didn’t have to chase them anymore- I knew where I stood. The same can be said for a person in the dating field that has come across rejection after rejection- you eventually build up an immunity to it. Suddenly the sting isn’t so bad and you kind of stop caring. In a way, you detach from the outcome enough that your ego will no longer be bruised if you learn someone isn’t into you. This is your ultimate point of power.
This is exactly the place I was in life when I reconnected with my now fiancé. We had known each other back in our grade school days, but never considered dating before. By the time I finally agreed to go on a date with him, I had reached my limit of trying to appeal to men. I was done pretending like I loved sports, or like I was way more successful than I actually was, or playing to the former NFL cheerleader thing- I was so tired of trying to be anything other than myself, so I decided to just be me. And what do you know, the old saying was true- when you’re 100% true to who you are at the core, your perfect person shows up and it’s always when you’re not expecting it to happen. The rest is history. From there, we were inseparable. We moved in together way sooner than I’d like to admit and within a year and a half we were engaged.
Now to the part you actually want to read about- THE ENGAGEMENT! Being an Italian girl, my dream has always been to be married in Italy. I dreamt of a very small wedding with only the closest friends and family in attendance. Something about a big wedding gives me extreme anxiety. The thought of all the people in the room looking at me in that moment of pure vulnerability makes my heart beat out of my chest. I know, I know, how could someone who has cheered for 60,000+ fans have a fear of being seen? Remember the key word here- vulnerable. I never ugly cried or made public vows at a Rams game, so it’s a little different ball game to have an entire crowd of people watching you have a tender moment with someone you love.
The funny thing about finding your person is what you’ll be willing to give up. Due to some logistics with getting family and friends with young kids over to Italy, my then boyfriend (soon to be fiancé, hold your horses) brought me down to reality by saying there was just no way to be married in Italy, but we could take a trip there together just the two of us and have an epic vacation. Obviously a little sour about it, I obliged. I agree that one day whenever we get engaged, I’ll have a wedding in our hometown so that all the people we love most can be there. So, he plans this perfect little vacation to Italy to try to makeup for telling me the wedding of my dreams is out of the question.
Of course I’m still beyond excited to be taking a trip to Italy with my boyfriend. The day comes and we show up to the airport bright eyed and ready to get there. Getting out of St. Louis was a little tough. A small storm rolled through and ended up delaying our flight to Newark which created a snowball of horrible luck. I’ll spare you all the travel details because that’s a story in itself. It ended up taking us three days to get to Italy. We had delayed flights, cancelled flights and missed connecting flights. There was a small thought in the back of my mind that maybe I would be getting engaged on this trip, but that all went out the window once we ran into all the travel troubles. We went in and out of security checkpoints multiple times and he never acted strange, so I knew there wasn’t a ring in his pocket. The airline also lost our luggage, which he wanted to leave- so again, you wouldn’t be willing to ditch your bags just to get to Italy if you had an engagement ring hidden in your bag. So, in my mind I was sure there was no engagement, this was strictly going to be a vacation.
Three days and a two hour car ride later, we finally make it to Italy. I’m sleep deprived, exhausted and crabby. But I’m quickly reminded that we have to get ready for a photoshoot I planned in Positano. You see, when I realized I couldn’t have my dream wedding in Italy, I requested that we take professional pictures there that I could use one day whenever he did pop the question. So the plan was to have these pictures blown up and decorating my venue one day for an Italian theme wedding. However, considering all the travel issues, I was pissed that I had to look somewhat presentable for this photoshoot.
I pull myself together as quickly as possible and we head out for the photoshoot. We’re taking pictures and my then boyfriend Joe says he has to go to the bathroom- totally typical for a guy, so I think nothing of it. He says he's going to run to a local shop to use the restroom and tells the photographers to take some solo pics of me while he’s gone that I could use for my website (yeah right). So he runs off. Ten minutes go by and I can finally see him running back to us. At that point, the photographer says he’s going to take some solo pics of Joe- so I stand over to the side and start taking in the scenery, completely unaware of what’s about to happen. Joe drops down on one knee and I froze. Genuinely surprised and happy as could be, I couldn’t even utter the word “yes”. All I could do was ugly cry.
After I pulled it together, the photographer suggested that we take some pictures walking through the streets of Positano as a newly engaged couple. As we rounded the street corner, I got the second biggest shock of my life. Joe had surprised me with my parents and sister, as well as his parents- they had been there the whole time. I’m a writer and I can’t even begin to put into words how happy I was and still am that they were all there to share in this moment. We’re both of Italian decent, so to have both Dad’s in the “homeland” experiencing Italy together was a memory I’ll never forget. I’ll share pictures below so you can see how stunning I am when I’m truly shocked. STUNNING.
As it turns out, our families had been in Italy for two days waiting on us to get there. Joe’s Mom traveled with the ring in her pocket, so there would be no chance of me finding it while going through security. So when Joe ran back to the bathroom, he was actually grabbing the ring from his Mom. I never knew he was such a smooth operator- the amount of effort that he put into this is amazing. It’s one of the many, many reasons that I love him.
I don’t want this post to be too long, I’m thinking I’ll do a video detailing more about how it all went down. What I do want to share with you are some of the most important takeaways from the experience. If you hadn’t noticed, my first book, Suddenly Single: Modern Tales of Fairy-Fails was published days before I left for Italy. In a ten day span I went from suddenly single to suddenly engaged and I know that has everything to do with finally being true to myself. When you stop pretending and let your walls down, life shows up and the things that you’ve always wanted can fall into place in the most amazing way possible. All the things you think will matter don’t. Like that small Italian wedding I wanted, I could care less now. My fiancé wants a big Italian wedding in St. Louis, so guess what- we’ve having a HUGE wedding just the way he wants it. I’ll just have to get over my fear of crying in public.
All of my fairy fails leading up to my ultimate fairytale made me who I am today and I wouldn’t trade even the worst of moments as a single girl. Without them, maybe I wouldn’t realize how lucky I am today. People change and evolve as years go by and I think 2019 was probably the biggest year of personal growth for me. I’ve learned that the world opens up when you take off the mask of who you think you should be and start living as your authentic self. Fairytales are real, but you may have to kiss a few frogs before you finally find that prince. But believe me, it’s worth the wait.
Michele is a former St. Louis Rams Cheerleader living in St. Louis. Follow Michele from the sidelines of the NFL to the sidelines of the modern dating world.