Chandler and Emily had planned a photoshoot with their friend Jevaughn for fun. It was for a "promotional Valentine's Day photo session" and they did not have any professional photos together so it sounded like fun. Little did Emily know, that Chandler had secretly reached out to Jevaughn beforehand in order to make this into a surprise engagement photo shoot. They had all gone to Chicago on that Sunday and spent the day roaming around the city and snapping pictures. Emily had secretly hoped Chandler would pop the question, but decided he probably wouldn't because the day was nearing an end. Then, to Emily's surprise, they were able to stop at London House Rooftop. This was a special place to Chandler and Emily since they had previously gone to this location on a couple of different occasions, mainly for the remarkable view. They ended up going up to the rooftop, which to their surprise, was EMPTY. However, it was very cold out that day. They then made their way to the beautiful Cupola on the rooftop, where Emily was told to turn around and face the city for a photo with Chandler holding her hand from behind. Chandler then got down on one knee behind Emily and as she turned around, asked for her hand in marriage. It was an incredible day.