Alesha and Kyle

How We Met

Kyle and I met at the nudging of our mutual friend, Nikki. Nikki is married to one of my closest friends, Katie, and worked with Kyle in Waunakee. About 9 months before we met, I was questioning my current relationship, and Kyle wasn’t having very much luck in the dating world, either. One night, Katie and Nikki met me at the dog park so we could walk, talk, and vent. Nikki off-handedly said, “I know you’re not ready right now, but I have someone for you.” I laughed it off, and we moved on.

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Right around the same time, Kyle had a very similar conversation with Nikki. She told him that she has a girl for him that would be a perfect fit. The only problem was, she was currently in a relationship with someone else. Kyle responded with, “So it sounds like you don’t have someone for me!”

Fast forward 9 months and some things have changed:
1) Kyle and I are both single
2) Katie and Nikki are a few weeks away from moving to Colorado

Nikki asked me if it would be okay to give my phone number to a coworker of hers – she wanted to make sure she made the introduction before she and Katie moved. Although I wasn’t really looking for anything serious, I trusted Nikki to know if someone might be a good fit, so I agreed. Kyle texted me, we chatted, and immediately hit it off! We made plans to meet up as a group with Katie and Nikki and a few other friends.

Some things about that first meeting:
1) I told Kyle about how Katie, Nikki, and I all had bladder issues while at a trampoline park. I now regret that decision.
2) Kyle tried to buy a round of drinks for everyone, but the bar’s card reader didn’t work and their ATM was broken. I had to buy the round, and Kyle was sure he’d never hear from me again.
3) Kyle did the splits at my insistence. He now regrets that decision.
4) Kyle asked me to go on a date with him.

Really, the rest is history!

Alesha's Proposal in Madison, WI

How He Asked

Kyle had a lot of grand plans for how he wanted to propose to me.

He had enlisted my best friend, Theresa, to suggest to me that we do a double date with her then-fiance, Aaron, and Kyle. We picked a day, and I checked with Kyle to make sure he was free. Of course, he was. We had decided to go to a restaurant downtown. Kyle’s plan was to have Theresa suggest we walk up to Bascom hill after dinner. I am a UW-Madison alumnus, and I had told Kyle that I never got my picture sitting on Abe’s lap at graduation. Kyle was going to make me get up on the statue, and then propose!

That didn’t happen.

The day Kyle proposed was rainy and humid, and I didn’t want to walk downtown in the rain. I suggested we pick a different restaurant, and Kyle seemed okay with that. Luckily for him, I suggested Cafe Hollander – the restaurant where we’d had our first date. His new plan was to suggest we get a picture at our first date spot, and then propose as Theresa snapped the photos.

That didn’t happen.

Kyle just couldn’t wait and wanted to do a photo before dinner. It was still raining, but we knew the rain was supposed to stop in the next hour. I adamantly refused to take a picture before dinner – in my mind, we both knew it was going to stop raining! Why would we go out in the rain!? After dinner, we went to a good spot for the photo, but there was a really weird guy standing a few feet from us yelling and waving. We think he was trying to get the attention of his family. Either way, Kyle decided maybe that wasn’t the best time to pop the question.

Our plan was to go to a bar after dinner to watch the big Mayweather vs McGregor fight. Theresa suggested we stop back by our apartment before going out again. When we got back home, Kyle called me over to him while Theresa and Aaron were out on our porch. I thought for sure he was going to say he didn’t want to go to the bar, so I immediately started saying “Yeah I don’t know if I want to go either-” and was cut off by Kyle taking my hands, and beginning to propose.

I let out a “What are you doing?!” before just shutting up and letting him finish. I said yes, we cried, and then we hugged our dog because he, of course, needed to be the center of attention. It was perfect.