As many who have tried online dating can tell you, it can be difficult to navigate through the sea of faces to find the right person, so sometimes we need a little help. Trey's friends Ansley and Maddie commandeered his phone, determined to find him the perfect girl on OK Cupid. They spotted her profile and swiped right, she liked his, and it was a match (78% to be exact). From the first message, they talked non-stop for two days until their first date at The Liberty in Midtown. He wanted you all to know that she was late but, to be fair, he made her come near his job instead of coming down to hers (not a very gentlemanly thing to do). They bonded over cocktails and conversation, which had many interruptions due to Trey's apparently tiny bladder (lol). Trey likes to brag about their '8 hour date' since they left the liberty to hop from one bar to another until they ended the evening with some dancing in the lower east side. They were apart for Christmas but chatted online regularly and spoke once when Ashley 'accidentally' called him. Once they returned to the City after Christmas, they got together again as she introduced him to her love of Groupon and discounted Restaurant.com gift certificates, exploring restaurants and activities in the city. He told her in their first messages that he was not a big fan Halloween which has changed a lot over the years. She loves making their costumes more intricate each year and he plays along with whatever crazy idea she has in mind. They have had many adventures together and can't wait to see what the future has in store!

They had planned to meet up after work that Friday by the Hudson River as they did many times to drink wine in the park before heading to an outdoor showing of the movie 'Sing'. Little did she know, Trey had set up this Friday weeks in advance, confirming several times that she wanted to meet him there on this day. Ashley went to Bed Bath and Beyond at lunch to get a blanket so they didn't have to sit on the ground and hit up CVS for some movie snacks. She showed up with bags full of stuff and drinking a protein shake. They sat down together on a bench near the water. He handed her a book, "The Story of Us", and she put down her shake (knowing what was coming). She read the book which contained their first messages, memories they shared and things he loves about her. The last page contained a proposal, they both cried and she said YES! A strange man came over and took their photo, "Can we get a copy?" she joked. That strange man turned out to be Trey's friend and future best man Horacio, so she did get that copy after all. After he popped the question, they both made calls and texts to family and friends to share the news, but Trey had one more surprise for her. He brought her to the place of their first date, The Liberty, where they were greeted by a group of over 30 of their friends awaiting their arrival (who had faked surprised reactions to Ashley's text messages). They celebrated with drinks and ended the evening with karaoke in true T&A fashion.