When Anthony mentioned to his friend Clare that he was open to set-ups, he didn't expect anything would come of it. But a few weeks later, she texted him that she had someone in mind: her then-roommate Jess. Clare told Jess that Anthony was kinda nerdy so she agreed to go out with him, but when she found out his name--the same name as her brother--she thought, "Okay, I'll only go out with him for one date." The two chatted on the phone for about 20 minutes, covering music, TV, and even establishing their first inside joke. They made plans to go out that Friday, March 3. But when Anthony started feeling under the weather, he asked to reschedule for the next week. Jess assumed he was faking it, but when they continued texting up until the date, she thought that might be a good sign.

With the first date now scheduled on a Wednesday night, Jess let Anthony know that it would need to end early, as she needed to be asleep by 9 PM in order to be ready for work the next morning. Anthony promised she would be sick of him long before then. Jess arrived 30 minutes early for the date because she gets nervous about being on time. She brought a book to read since she had extra time and ordered a drink. Anthony arrived about 10 minutes early and was seated at a table by himself. He decided to wait to order even though happy hour was about to end. When 8 minutes had passed, he ordered his drink, after which the apologetic host informed him that Jess had been seated long ago, leading him to her table. Jess put her book away, telling Anthony she had brought it in case he was a "dud." She still considers this her best joke to date. Anthony smiled, knowing that they were in for a good date. The two began talking and it felt like no time had passed at all when Jess checked the time: 9:13 PM.

As Anthony put his proposal plans in motion, he wanted to pop the question near Navy Pier, where the two had had a memorable fun afternoon date. But how to get Jess there? He told her that he'd made a brunch reservation downtown, and they got ready to head out when Jess inexplicably put her hand in his coat pocket and felt the ring. (She insists to this day that she was searching for gloves in his pocket, despite never having seen him wear them before.) They paused, speechless--Jess began tearing up, but Anthony took the fact that she wasn't running away as a good sign. They then took a half-hour bus ride where they barely said a word. After taking some uncharacteristic selfies in front of the Chicago skyline, Anthony got down on his knee and asked Jess to marry him. Even though she had seen it coming, Anthony managed to pull off one surprise, as he pointed towards their friend Becca taking photographs. "I'm crying!" Becca exclaimed. "Me too!" Jess responded. Becca led the elated pair on a short photoshoot before they finally headed to brunch.

We are so grateful for you to join us for our wedding!