How Andrew Asked me Out

One of my favorite stories to tell people is the story of how Andrew asked me out for the first time. He always rolls his eyes and acts like he hates it, but he knows it’s funny, too. I’m sure I’ve not shared this story on my blog so this is long overdue!

Andrew and I have known each other since middle school, but we didn’t really get close until freshman year of high school. We had several classes together and began to get to know each other better. We bickered all the time because we were both too stubborn to admit when the other one was right. I had a few friends who would always tease us about “dating” and I would roll my eyes and say, with gusto, no.

He slowly became one of my closest friends… and then suddenly I began to see him as more than a friend. All of my friends’ teasing had some validity to it. I think this happened to him around the same time, because I remember him being a lot sweeter. He would text me good night and good morning, and just the little ways he said things to me showed me he cared. I confided this in my best friend, Becky, because I was a bit embarrassed at first with all my friends teasing and such. I promised her not to tell him, because they were also good friends, but also because I really didn’t think anything would come of it.

Little did I know, Andrew told Becky that he had feelings for me but made her promise not to tell me. (I know, so very high school, haha!) I laugh now because I think of what a situation we put her in! She wanted to tell both of us but didn’t want to go back on her word, so she repeatedly encouraged Andrew to ask me out.

Andrew and I lived about a five minute drive from each other, and there is a park that is right in the middle of both of us. We started meeting at the park and taking walks and just talking to each other. One day, he told me that he had something important to ask me. This piqued my interest and I immediately thought, he has to ask me out! Almost giddy with anticipation, we met at the park.

He didn’t act like anything was out of the ordinary. I repeatedly asked him over and over what he wanted to ask me. He kept dodging my questions and I was becoming more and more impatient. Besides, I was fifteen and a boy I liked might ask me out!

After what seemed like hours but was probably only fifteen minutes, I threatened to go home if he wouldn’t just tell me what we were here for. (I know, so dramatic.)There was a hesitation, he stopped and turned to me, and I knew, I knew this was going to be The Moment. He opened his mouth and spoke the words that I will never forget:

“Becky wants us to go out.”

I am not sure there has been a more awkward time in my life than the next thirty seconds of that conversation. That was not what I was expecting him to say.

I finally found some words. “Well… do you want to go out with me?”

Shrug. “I guess.”

Well, that really boosted my confidence. I don’t even remember how I responded. He walked me home and as we stopped to say goodbye, I asked, “So… are we dating?”

“I guess.”

Little did I know that those two noncommittal words would amount to so much more later on. I mean, I married him so I guess we turned out alright. ;)

13 thoughts on “How Andrew Asked me Out”

  1. Oh, my goodness.
    This was a great story! And how cute that you have such early memories with your husband. I mean, you knew him during his awkward pre-teen and later awkward high school phases. Too cute. I’m still learning things about my boyfriend and I’m constantly asking him for stories from his younger days. XD

    I can’t wait to hear more stories. <3<3

  2. It’s cute how long you and Andrew have known each other! At this point, wouldn’t it be half of your life? It’s cute how you both slowly got close because of being in some classes together. Haha, school counselors/schedulers work some pretty neat magic XD.

    The way you both told Becky about your feelings is pretty funny. It’s good that Becky tried to keep her promise. Haha, I can’t believe you threatened to tell him that you would go home XD. I don’t think I can ever do that with any guy I liked.

    “I guess” – trademarked by Becca

  3. That is such a wonderful story <3
    I met my husband at my first full time job !

    We started really dating in 2009 and married in 2013. <3 We are still going on strong. May you and Andrew continue to be strong!~

  4. BRB, I am forever laughing at this story and how TYPICAL it is of high school boys. Reminds me of my high school boyfriend pulling that sort of thing on me when I asked “Why do you like me?” and his answer was a “I don’t know.”

    Such a cute story, though! I’m also laughing at the irony of you two liking each other, and poor Becky had to be the one caught in the middle of not saying a single word to either of you XD; And when he said Becky wants you two to go out . . . HAHAHAHA!

    Thank you for sharing this! This post just made my night, hahahahaha!

  5. lolol omgomggg this was so cute. ? And very “high school” indeed… but lots of crushes-turned-relationships end up something like this anyway. Most of my early boyfriends (that I had during school or at least started in school) asked me out in this kind of way, or a mutual friend put us together and made us talk or something really silly like that.

    I’m glad you told this story, it was definitely very overdue haha. We all have our little stories about how stuff began. I think it always starts with that little bit of flirting – with one of my exes, we used to try and step on each other’s feet under the desk, and that was how things started. I was seeing this guy for a short amount of time but we started when we got chatting at an event, then we started to joke about kissing and it happened, so… ? As for me and Nick, there is not really a big cute story behind how we “officially” got together but some corny words were said, like how we’ll promise to be together ~forever~ and stuff like that. ?

  6. Aww! I love this!

    The story of how Andrew asked you out is very similar to the way Tyrone and I started dating in that we’d known each other since primary school but it was only towards the end of high school that we became close friends. Tyrone told my best friend that he had feelings for me, and she revealed this to me when I told her I had feelings for him.

    But then I made it super awkward and asked him if he liked me, unbeknown to the fact he had a plan to ask me out. Anyway, it was awkward but we stumbled through and he we are 7 years on.

  7. What a cute story! I love reading stories like this of how couples came to be. How neat of it that you two knew each other through so many years without much of a thought to be together then at the same time you both decided, hey I kinda like him/her.

    Thank you for sharing this story. Congratulations to you two and may you share many, many more years together.

  8. Oh my gosh, this is such a cute story! The way everything unfolded and the response “I guess” was indeed very high school, but I still love it! Haha! It’s so nice that you guys are still together after so many years and I hope you have a happy marriage! ;)

  9. That’s hilarious. ? It’s definitely “so high school”, but how did you guys develop beyond his initial “I guess”? I ask because it would have turned me off. ? (And relationships fascinate me.)

    (You also don’t have to answer, of course. ?)

    1. You know, it’s curious that I’ve never even thought about me turning him down after him showing his reluctance. I think at that time I was very infatuated with him and the idea of having a boyfriend since he would be my first. But I think the big thing here is that we were best friends. So even if I wasn’t sure how much he was interested in my romantically, I knew he still liked me at least as a friend and that was comforting to know.

      It was really just getting past the initial awkwardness since this dating thing was so new for the both of us. He was scared to hold my hand at first. XD And like I said, we were already close friends so that gave us a really good foundation.

      I hope that answered your question. :)

  10. Aww, I liked reading this! I think stories about how couples go together are so fun to read :) I think that’s great that you guys became close friends over time before dating. Also, that’s so funny how both of you told Becky the same thing, and how “The Moment” ended up being “Becky wants us to go out”, hahaha. At least it was memorable! Thanks for sharing this with us!

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