Top Theme Image
Top Theme Image

Jake & Bailey

August 14, 2026 • Madison, WI

Jake & Bailey

August 14, 2026 • Madison, WI

Our Story

Picture of Our Story

They say, “you may have already met your soulmate, but you just don’t know it yet!” Well, that couldn’t be more true for us! We knew each other for over two years before we started dating, and from there our story began! As in most cases, there's usually two sides to every story......

Jake’s Side:

I was a regular at Red Rock, and Bailey was always behind the bar with her smile and quick wit. I’d swing by with friends, and she’d always hook us up with great drinks and even better conversation. I thought about asking her out from the moment I saw her, but I didn't pull the trigger... partly because I didn’t want to ruin the vibe, but more so, I didn’t want to mess up and lose the drink deals (though I was confident we both felt something there)! Then the pandemic hit, and everything came to a halt. During the downtime, I bought a boat and spent a lot of time thinking... with a little push from a friend to make a move, HE (thanks Jeff) invited her out boating with us! I was stunned when she agreed and finally decided it was time to speak up. After a relaxing evening out on the boat with friends (and Gus), I finally asked her out... I could hardly believe it, but she said yes! For our first official date, we, once again, planned to go out on the lake. I still remember picking her up... backing down this long, narrow, winding road... just hoping I didn’t screw it up. After getting on the water, we spent the evening getting dinner at Buck & Honey's, playing cards, and having a few drinks. Both of us held off as long as we could, not wanting to call it a night, but the drinks kicked in, and, well, there's no bathroom on the boat... But here we are, together ever since!

Bailey’s Side:

I knew Jake as one of the familiar faces who would come into Red Rock most weekends. He was always friendly, funny, surrounded by friends, and never skimped on the tip (so naturally, I made sure he got the best drink deals)! I never thought much of it... Honestly, at that point, I'm not sure I even fully knew his name. I'd just look for a tab that started with "J" (Jacob or Jeffery). Then Covid came, and that put everything on pause. The first night he came back downtown, I didn't even recognize him with the grey hair! (I still say that's what got me hooked.) Anyway, Jeff asked if I wanted to go out on the lake with them, and of course, I was in! To be honest, I think this was the night I was finally able to put names to faces. I had no idea whose boat I had agreed to go on, nor what I was getting myself into. However, it was genuinely a great night, and I was surprised when Jake asked me out after it was over! Later that week, Jake wanted to go back to the lake and said he would pick me up. I offered to walk down to the main road, but he insisted on doing it right and picked me up at my door. I didn't have high hopes- I thought for sure I'd watch him try to back his boat down my one-way/no-margin-for-error/half-mile road, get "the ick", and it would be game over. However, he executed it flawlessly! The night was perfect; neither of us wanted it to end! Since then we have taken on life side by side- the highs, the lows, and everything in between. Last October (2024), Jake brought me out on the boat, back to the same spot. I might have thrown a hitch in his plan... He mentioned there was wine, but the only cup he brought said "Future Mrs.". Well, my impatient self couldn't understand why he wouldn't give me the darn cup right away! So, he had to hurry his plan along... He got down on one knee, proposed, and we relived our first date! The evening was perfect and made for an unforgettable night! My note to guys: BUY THE BOAT!

Now, here we are, ready to tie the knot and celebrate with all of you, as we begin the next chapter of our story!