After swiping right on Bumble, Tripp took April to Luca on their first date. Over a bottle of wine, they got to know each other, discovering many shared interests including their precious doggies, beer, the beach, and live music. The time flew by! After finishing their dinner, they ended their date in hopes for another. A week later, on their second date, they split a Froze at the Park Bar. On their third date, April learned Tripp's "real name" was Donald Eugene Horn III, while sitting outside at The Fridge. Tripp pulled out all the stops for their fourth date, snagging pit tickets for Zac Brown Band at Hershey Park Stadium. He was trying hard to win April's heart - and it was working. Although the pair wouldn't call each other "boyfriend/girlfriend" for a couple more months, they had a feeling it could last!

On their second trip to the Finger Lakes, Tripp and April made it a true family affair and brought Jax and Lucy along for the fun. After four days of hiking trails and trying new wineries, the car was packed and they were ready to hit the road. With an AirBNB overlooking Seneca Lake, Tripp persuaded April to take one last walk down to the dock. It was freezing and about to snow, but she couldn't say no. Down at the dock, while April was distracted by the clear water and beautiful view, Tripp got down on one knee. It was so sweet and so perfect: she said yes! After lots of hugs and kisses, and some more hugs and some more kisses, they practically ran back up the steps to share the good news with the dogs: Mom and Dad are getting married! Everyone was on Cloud 9 and couldn't wait to share the news with everyone else at home.