As a freshman in college, Gwen was always open to chatting up a cute boy. While hanging out in her dorm, one of her friends was on FaceTime with her boyfriend from home (shoutout Amber & Colin) and it just so happened he was sitting next to his roommate on the bus home from a football game. No, they didn't play college football ... but they did play the trumpet on the sidelines! Gwen's cute boy radar went off and she boldly asked to add him on Snapchat. After a few rather unexciting pictures of faces getting sent back and forth and then a long stretch of silence ... Gwen deleted him. Her exact words were "Who the heck is Kyle? I'm deleting him." Not long after, the same friend group of Curry College girls went to visit that same home boyfriend (Colin) at his super cool, big, party school .. UCONN! All the girls unloaded their bags into the tiny freshman dorm room and got ready for the weekend. While taking a look at the tasteful decorations picked out by 18 year old boys, Gwen studied the photos on Colin's roommate's wall. Pictures of family vacations, ski trips with friends, and a really cute dog covered the wall. Not even remembering her brief conversations that she had with Kyle previously, Gwen asked Colin which person in the pictures was his roommate. Once identified, Gwen replied as expected ... "Oh! He's cute!" Turns out, Kyle would not be at school this weekend because he was away skiing with his friends, so Gwen was left to look at pictures on the wall and party on without him. As the semester went on, Kyle remained "the cute boy on the wall" in Gwen's mind. Now this is where it gets good! While sitting in on another FaceTime call with her friend and her boyfriend, Gwen asked if Kyle was around ... he was! Gwen asked to talk to him and immediately said "Hey! I think you're handsome!" Kyle's genius reply went something like "You're not so bad yourself." After this conversation, Kyle and Gwen officially began to snapchat and text every day, with their first date planned for Spring Break. After just one date, Kyle was definitely in love. After months of talking, dating, and asking .... Gwen finally agreed to be Kyle's girlfriend! After about 7 years together, including moving in together and adopting their dog, Ellie, Kyle proposed on Gwen's favorite beach in Charlestown, Rhode Island. It was sunny and freezing and perfect.