Scrolling on a dating app. Gabby was trying to get a free meal before Covid shut down all the restaurants again. She suggested to Jeff that they should go out for dinner. Jeff agreed and made a reservation at a seafood restaurant, not remembering Gabby only eats chicken. All went well and they ended the night with an awkward side hug.

Jeff tried to propose 3 times before actually asking. First attempt was a romantic surprise trip to Harpers Ferry. As they walked up the trail to the scenic lookout Gab made it known that she wanted Jeff to do "nothing weird" because she was crying from getting a bug in her eye. The next attempt was at a vacation to Disney World when again, Gab foiled Jeff's plans by never going on a private walk through the gardens when Jeff asked. The final attempt was at Gunpowder Golf Course. A place they often spend their summer weekends. Looking over the 16th hole.