Online Dating -> Engaged! Here’s My Story

This post is they type of thing I read a lot of about 3 years ago when I was first getting into online dating. I was curious about how it worked, and I wanted to know more about the type of people who *actually* met someone on a dating site. So I’m typing it up for anyone out there who would like to hear about the process of going from online dating -> engaged!


First of all, I should say that the online dating process that led me to my fiancé was my second attempt… The first time I tried online dating was when I lived in downtown Chicago after college. That time didn’t go so well. I met a couple weird people. Ha. I don’t think that I was emotionally ready to be seriously dating. I didn’t give it much effort, either, so the outcome wasn’t anything to talk about.

But this time was a different story, because it’s how I met my fiancé! This is how it happened:


I was approaching my first winter break of graduate school in Austin, TX. I went to a small private school for my undergrad, so I was unaccustomed to the 6+ weeks of winter break that I had during grad school at a large state university. I needed something to do during break other than practice my violin and watch netflix, so I decided to try two different “hobbies.” The first was training for a marathon (which I ran the following February!), and the other was trying online dating.

I’m a planner, so I totally did my research before I signed up for an account. I know…it’s kind of embarrassing. Some people are great at dating, but let me tell you that I am not that girl. Nope. I had done very little dating in my life, and I wanted to have fun with the process and not be freaked out the whole time, so I prepared. I read dating books, (<- uggh, so embarrassing. But true.), I researched which dating site to use, and I read way too many online articles about how to fill out an online dating profile with cheesy titles like “6 Things To Put On Your Dating Profile To Make It POP!” and “15 Things To Never Say On Your OKCupid Profile.”  IknowIknowIknow… I told you that I am not a natural at this!

I picked OkCupid because it was 1) one of the most popular sites (more fish in the sea, eh eh?), and 2) it was FREE! (#brokegradschoolgirl) This was several years ago, so I can’t say what OkCupid is like right now, but I’ve heard from a couple sources that’s it’s been going downhill…


wish I had saved what I put on that profile, because I would love to read it now and laugh! (I’d also love to see my message thread with Nate at the beginning, but I don’t have that either.) But being a girl on a dating site is an easy way to go on a lot of dates in a short amount of time. And I had a blast! Ha. That December, I sorted through a bunch of messages. (Some were kind, some not so much…if you’re using a free dating service, be prepared to filter through a lot of messages. It’s sad how people assume they can talk to others when there’s a computer screen between them.) I went on a lot of dates, and although no sparks flew, I met some nice men and got to experience a lot of new coffee shops and bars and restaurants in Austin, a city that was new to me at the time.

One of the challenges of online dating is to know when to quit. It’s a pretty time-consuming task, which is why I did it when grad school was out of session. It’s not like dating IRL, when something happens every few weeks or months or years…online dating is a constant fire hydrant of attention and messages, new profiles to look at and potential dates to message. It got a little exhausting. I decided to stop when school started again, which was mid-January.

But there was this one guy I had been messaging who I still wanted to meet in person….


Nate messaged me, and we instantly hit it off, messaging back and forth for a couple weeks. I knew that I wanted to meet him, so I messaged him my phone number and told him I’d be deleting my OkCupid account now that school was back in session for the spring semester, but he could text if he wanted.

We texted for a couple more weeks before we finally went out for our first date. I’ll say that, with online dating, expectations are set pretty low for first dates. It’s kinda easy to lie about your appearance/personality on a dating profile. (Everyone who’s tried online dating has a story about that one date whose profile picture was actually 5 years younger or 30 pounds slimmer or a head of hair fuller than their actual appearance, y’know? Haha.)

Our first date was at Craft Pride on Rainey Street in Austin, TX. I knew I liked him a lot from the second we sat down across the table from each other with our flight of beers. That was something I hadn’t I hadn’t felt with any of the other dates. I remember that exact moment when I thought “this one is different.” 

(Ha! It sounds cheesy! I just erased that sentence and tried re-writing it, but I can’t explain it any other way… If you’ve met “your person”,  you know exactly what I’m talking about!)


The story goes on from there through several years of dating, a proposal, and now planning a wedding! After the initial meeting process, there’s nothing about our dating story that’s different from two people who might have met in person instead of from a dating site. Sometimes we talk about how we met and think, “isn’t it funny that this all started with online dating?” I also often think that if I hadn’t decided to try online dating that month, I most likely wouldn’t ever have met Nate.

{all photos from sam hugh photography}


So that’s my story! I’m headed to enjoy a yoga class and then do some violin practicing for a weekend gig. It’s finally getting cold in Austin this weekend, and I couldn’t be more excited!! My cold weather clothes have been waiting patiently in my closet for weeks!

Have a wonderful Thursday!


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7 years ago

Seeing as the last time I saw you was right before you took off from Chicago to Austin, was wondering how you two’d met!
I also tried OKCupid for a month about 2.5 years ago. I wasn’t actually ready to date but it was nice to find something to fill the time so I want sitting around at home alone. I think I went on 4 dates and they were all either awful or lackluster. But then someone I’d met several years prior saw my profile there and, realizing I was now single, messaged me on Facebook asking how I was doing. He didn’t tell me until later that the reason he’d reconnected was because he saw me on a dating website haha! It took a few months for me to be open to the idea of dating, but now we’ve been together 2+ years – so I’m also glad I gave OKCupid a try 😀

7 years ago

Beautiful story, Kelsey! I am so thrilled that you are happy with a wonderful future together!

7 years ago

[…] on Rainey street at Craft Pride, the bar where we had our first date (not where we met, because we met online), and the other location at The Long Center where Nate will sometimes come to watch me play with […]

7 years ago

[…] online dating profile so I could focus on my spring semester of grad school. And that’s how I met this man in a Texas craft beer bar on Rainey street in Austin, TX. And in just 53 days, we’ll be hosting a bunch of our friends in family for a big ol’ […]

6 years ago

I’m just now reading your ‘About’ section after months of following you on IG: I met my fiancé through OkCupid too! Another success story: love it. We met in March 2013 and are getting married next March in Austin!

Reply to  Kelsey
6 years ago

That’s our wedding date in 2018!! Too funny. It’s coming up sooner than I’d like to think about: so much to do!

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