Cathy and Jeff

How We Met

I had just gotten out of a long-term relationship and definitely wasn’t looking to get into anything serious. My girlfriend had suggested that I try a couple dating apps to get back into the game. I wasn’t about that Tinder life so she suggested Hinge. I was hesitant but after some much-needed encouragement, I caved. You get matched based off your Facebook friends so that made me feel a little better.

Jeff was one of the first guys I swiped right for. He started messaging me with a joke of all things. I still remember it till this day. “What do you call an alligator wearing a vest?” I didn’t know, of course. “An investigator!” The rest was history.

He was the one and only guy I met up with through that app. Our first date was on the most freezing day in February. We went out for drinks (his friend told him there’s too much pressure if we did dinner ha) and ended up staying out for hours trying to find places we could go to make the night last a little longer. It was so cold that when we got to my car, I was desperate to sit on my heated seat that I gave him a quick kiss. So I guess you could say I made the first move. From that night on we saw each other as much as possible and texted practically all day every day. I still can’t believe we didn’t get sick of each other.

So here we are almost 4 years later. We moved in together after 7 months of dating, have shared two apartments, have an equal obsession with Netflix binges, and laugh every single day.

How He Asked

Jeff and I had been planning our first trip to Italy for two years before the day finally arrived. 10 days of eating all the pasta, pizza, gelato and drinking all the wine we want. Months before we had talked about getting married and such, as all serious couples do at some point. We even went to look at rings – Jeff knows how particular I am so he wanted to make sure he would get exactly what I wanted. But he expressed that he wanted to wait till after he got a bonus or promotion at his job. We agreed it wouldn’t happen for a bit.

Flash forward to Italy. Our first two days in Florence were amazing. I was excited because our last full day we planned a wine tour through Tuscany. Jeff got me into wine more than I had been, so now we’re both pretty much wine snobs. We arrived at the meeting point for our tour and while waiting for our guides, we started chatting with these two couples around our age. Jeff can literally talk to anyone so this didn’t surprise me. I went to go show our ticket vouchers while he kept talking to them couples, since we thought they would be in the same tour group as us. We realized that they were placed in another group and we noticed one of the girls call over to us apologizing profusely that they wouldn’t be in our group. I remember thinking that was odd since we had just met them, but brushed it off as her just being super nice.

Cathy and Jeff's Engagement in Tuscany, Italy

So we hop in the van with a few other couples and started our journey through the green, lush fields of Tuscany. Jeff, of course, struck up a conversation with one of the women sitting next to us. She had asked if we were on our honeymoon (ha!). We arrive at the first winery of the day and make our way into the grand villa. Everything was so beautiful, from the endless flowers to the building’s architecture. As we stood there listening to the history of the villa, I remember thinking how happy and lucky I felt to be experiencing this with the guy I love.

We headed up to the rooftop terrace and I felt like I had to stop and take in the view. It was breathtaking. After a few moments, I suggested that we ask someone to take a picture of us. We start walking over to the corner where another couple is taking shots and one of the women jumps at the chance to take our picture. Weird I thought but brushed it off. I stand next to Jeff and as I’m smiling I hear him apologize to the woman that she’s going to have to take more pictures than she bargained for. In my head, I was like we only need like two shots.

Marriage Proposal Ideas in Tuscany, Italy

The next thing I know he’s down on one knee. All I remember saying is “What are you doing? Get up, you’re embarrassing me.” It hasn’t processed yet what is happening because I’m still confused and don’t remember hearing a word he said because I kept asking “Is this really happening? Are you serious right now?” All I remember from his spiel is him saying “You’re my person. I want to spend the rest of my life with you.” Of course, I lost it and the tears started flowing. The next thing I know I’m giving him my right hand (what a rookie move!) and not even remembering to say yes. We spent the rest of the day in complete bliss – with the wine of course!