I Helped Plan My Own Engagement & It Still Felt Straight Out Of A Tinder-Ella Story

Courtesy of Theresa Holland

I guess you could say I helped plan my own engagement. No, I didn't help to plan my proposal (that part was a surprise), but my husband and I did collaborate on when we wanted to get engaged, what my ring would look like, and how long we wanted to be fiancés before making it all legal. We are, and always were, a team. Getting engaged was just one of our many collaborations.

I met my husband on Tinder. I am the first (and only) person he ever met up with through a dating app, and he often brags that he got super lucky on his first try. "One and done, baby!" he'll say, with a laugh. I, on the other hand, met up with roughly 20 matches before my final swipe-right. But I'm equally proud of my determination to keep going out on first dates until I met my person.

Courtesy of Theresa Holland

On our first date, we met up at a cute little bar in Portland, Oregon. We drank cocktails, munched on grilled cheese sandwiches, and discovered how similar our families are (he is one of three brothers, and I'm one of three sisters). I was 26 years old at the time, and he was 29. We were both working jobs that we cared a whole lot about. Through chatting, we realized that we saw our life paths going in the same trajectory. It felt like kismet: We shared plenty of hobbies, and perhaps most importantly, similar goals. I know it sounds cliché, but that night, the stars truly felt like they began to align.

After that, our relationship never felt stagnant. For example, he met my parents on our second date (totally weird, I know, but the reason this happened is another tale for another time). Meeting my family right off the bat accidentally propelled us forward. If I had a family event on the calendar, I'd invite him without agonizing over whether or not it was too soon. Through mature, honest communication — yawn! — we quickly established that we both had our eyes on the serious stuff: marriage, a house, and eventually, kids. Once we agreed that we'd do these things together, it made our conversations about the future, well, easier.

He told me he loved me for the first time after I suggested that we stay in, watch the Trail Blazers game, and order pizza. It was such a goofy moment, but I could see in his eyes that he meant it, and I returned the sentiment. Shortly after, when we were canoodling in bed, I looked up at him and blurted out, "I would marry you." To my delight, he responded with, "Yeah! I would marry you too." It was short, but sweet — direct and to the point. With marriage mutually in mind, we began openly planning our timeline. The logical next step seemed to be to shack up, so we discussed moving in together. After six months of dating, we signed a lease.

Was everything always smooth sailing? Hardly! We definitely disagreed, and sometimes fought, about exactly when or how we would take each step. We got into heated arguments that lasted for hours about how long we should wait to get engaged. We discussed how many months it would take us to save up for a wedding. We had mutual freak-outs about how on earth we could feasibly put a down payment on a home. We were scared, but we worked through our fears together. It wasn't always easy-peasy, but each decision was collaborative — so, why would our engagement be any different?

About three months after moving in, we went ring shopping to figure out the right size and style for my engagement ring. (This was his idea, and I gleefully obliged.) We began talking regularly about when and where we wanted to get married, and counted back from there to determine when the best time to get engaged would be. We crunched numbers, talked dates, stressed over the expense of a wedding, and eventually settled on the spring of 2017 as the right time to get engaged. This would give us about a year to plan and save up for a destination wedding. Planning things out before he put a ring on it gave me confidence about our future and made me feel like we were truly equal partners.

OK, the element of surprise was somewhat gone — but not completely. For example, I knew a proposal was on the horizon, so every time we went hiking, I'd be looking over my shoulder for a hidden photographer (I'm such a millennial). But we didn't get engaged on a hike. When we went out for a fancy Valentine's Day dinner, I was pretty certain it would happen then, too. We didn't get engaged on Valentine's Day either.

Courtesy of Theresa Holland

It was a Sunday, and he had gone to have brunch with his brother. I was working out on the elliptical machine in our apartment building, when I got a text. "Don't make dinner plans tonight..." I texted him back saying, "OK. Should I shower?" I'm usually an every-other-day showerer, except for special occasions. He confirmed that yes, I should bathe before dinner. "Be ready at 5:00 p.m.," he said.

Since I knew there was a total possibility that tonight was the night, I showered, shaved my legs, blow-dried my hair, and put on a full face of makeup. He called an Uber, and sneakily told the driver to keep our destination a secret.

We were dropped off at the little bar where we met on our first date. Once again, we drank cocktails and ate grilled cheese. I was expectantly beaming, and he was killing time. Later, he confessed that he was purposefully trying to drag things out so that I'd second-guess myself. And drag it out he did.

Eventually, he pulled a little white box out of his jacket, held both of my hands, told me how much he loved me, and asked me to marry him.

I don't remember exactly what he said — I think I blacked out over sheer joy and excitement. I didn't fall over in my chair out of shock, but I wouldn't have had it any other way.

All this talk about timelines might sound a little rigid, but I've never felt that way. My now-husband and I do plenty of spontaneous things, but as cheesy as this sounds, sharing goals and co-planning our lives is what truly makes us a power couple.

Getting engaged was not something that I wanted sprung on me. Frankly, I couldn't imagine dating someone and not discussing a shared future. Surprise proposals may seem to work out in rom-coms, but having a hand in planning my engagement was my version of a fairytale ending — a real Tinder-ella story, if you will.