That Awkward Moment I Asked Him To Be My Boyfriend

So, if you read my last Wedding Wednesday post you might recall when I asked Mason to be my boyfriend he said no. But this is a wedding post, so obviously we’re engaged now and I did manage to convince him to be my boyfriend, right? Read on, my friends.

Christmas 2014

While home for Christmas, we texted almost non-stop. We said a lot of cute, corny things to each other like this:


And yes, he was in my phone as “JC” because I didn’t want anyone at work to know I was seeing him yet. What if I turned out to be wrong and there wasn’t actually anything special between us and we went our own ways after his internship ended?

Yeah, right.

My dad noticed how much I was texting while I was home for Christmas and I saw him glance over at me more than once with that tiny worry line forming on his forehead. Here’s the thing: My dad is the one who I ran to at 17 crying when my high school boyfriend told me he thought we should “take a break.” My dad is the one who comforted me at 19 when my college boyfriend took a similar route. My dad is the one who took me to coffee early in the morning when I was a 23-year-old crying wreck, reeling from an awful experience with my then-fiancé and his family. And my dad was the one who managed to get me in the car for a long drive to talk after I went through with that marriage anyway and then saw it come to a sudden end.

Basically, my dad had reason to worry about what I might be putting myself through next.

“Don’t worry, Dad,” I still remember the exact words. “This is a good one.”

New Years Eve 2014

After barely eating for four days, I could finally fit into the tiny pink and silver dress I bought from Forever 21 for my first public outing with Mason. We took some tequila shots and went to a huge New Years Eve party in the Fremont neighborhood of Seattle.

New Years

Our first photo together, New Year’s Eve 2014.

It was a bizarre night. First of all, my ex-boyfriend was there and I had a sudden urge to go up to him and tell him I didn’t like the giant bushy beard he had grown since we broke up over six months before. Yes, it was petty. Yes, I did that. Second, one of our coworkers was there — one who sometimes acted as Mason’s supervisor. Mason and I spent the night strategically dancing and talking and hanging out wherever my ex and his sometimes-supervisor weren’t.

Then, just after the midnight kiss, overcome with happiness and drunk on love (*cough* tequila *cough*), I looked up at Mason and said, “You should be my boyfriend. Do you want to be my boyfriend?”

“No,” he said with obvious hesitation. “Let’s talk about it tomorrow.”

CRUSHED. But I played it off, you guys. I was totally the chill, fun, cool girl who didn’t really care and definitely was not looking to fall in love and marry him someday and, who knows, maybe even have his babies.

New Years Day 2015

When I saw him the next day, I continued to play it off.

“Remember last night when I told you that you should be my boyfriend?” I said with a laugh. So chill, you guys. I’m a cool girl.

“Yes,” he said, seriously. “I said we should talk about it tomorrow.”


“Well, it’s tomorrow. Do you want to talk about it?” he asked.

“Okay.” I was so nervous.

He looked at me and said, “Do you want to be my girlfriend?”

I laughed at him, so confused. I asked, why did he say no last night?

“I didn’t think it was a decision we should make after that much tequila,” he answered.

I was impressed. This younger man who came out of nowhere while simultaneously living a life very connected to mine was more thoughtful, deliberate and intentional than I could have imagined. He showed he was able to provide a safety buffer around my impulsiveness without smothering me. He was a good one. And now he was my boyfriend.

Best of all, now he is my fiancé.


Engaged 10/25/17 – Brooklyn, NY



5 thoughts on “That Awkward Moment I Asked Him To Be My Boyfriend

  1. Zoe says:

    I love this. Such a great post! And congrats to you both. I think most decisions are better to be made the day AFTER the tequila 😉

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