In May of 2021, Bridget had freshly moved home to Chicago for the summer as she prepared to start PA school in August. On the first weekend back home, Greig Dimailig organized a group of friends to go out for drinks - one of those friends being Charlie Titzer. Charlie extended the invite to his older brother Bobby, who decided to tag along to a pregame in the Corcoran's basement.

After the pregame, the group made its way into the city to check out a few bars. Bobby decided that the bar they were at was not nearly as fun as the one his coworkers were currently at. He rounded up the group in an uber to Big Joes Bar where he promised we would experience a rowdy turtle race. Unfortunately, we got there 2 hours after the last race... With no racing to enjoy, Bobby and Bridget struck up more conversation instead. The night ended with the two sharing their first kiss on the corner outside of Big Joes as they waited for their uber back to the suburbs.

The rest of the summer of 2021 was filled with many dates around the city. Unfortunately, there was a glaring end date for the relationship - Bridget moving back to Missouri in August for PA school. The two decided it was time to say goodbye and shared their "last" date at Pinstripes for bowling. However, neither Bridget or Bobby decided to stop calling or texting each other despite the new 400 miles between them. For the next 2.5 years, their relationship continued to grow via monthly visits, endless facetimes, and LOTS of Netflix party movie dates. In December 2023, the two were finally reunited back in Chicago and moved into their first townhome ... this time, with no end date :)

On August 10th, 2024 there was not a single cloud in the 80 degree sky. Bobby had a full day planned for Bridget, but was keeping each activity a secret. They woke up and made chocolate chip pancakes, which was followed by Bobby telling Bridget they were going down to the river. When they arrived, their first stop was City Winery where they shared a glass of Sauvignon Blanc. They then walked further down the river to Beatnik for a late brunch (and another glass of Sauvignon Blanc of course). When they finished brunch, Bobby explained that they would need to kill some time before calling an uber to their next secret location. Little did Bridget know, their walk around the river to "kill time" was walking her directly to the spot of their engagement. A photographer stopped the couple and politely asked if he could take some test shots as he waited for his clients to arrive. As soon as the camera started clicking, Bobby got down on one knee and popped the question! With the biggest smiles and excitement, the two spent the rest of the day celebrating at a surprise engagement party at Sully's House with their friends and family from near and far.