Jason and Drew's first date was at Cuba Libre in DC in September 2018. During their initial banter, Jason casually mentioned that he liked rum. Picking up on this little detail, Drew very thoughtfully researched and found Cuba Libre, which offered a large variety of rum flights to choose from.

Unbeknownst to Drew, when Jason said he "liked rum," he was really just referring to his go-to bar order of bottom-shelf rum and Cokes (oh, college). He did not have the heart to mention this little fact until they were at Cuba Libre working their way through rum flights that - turns out he actually isn't the biggest rum fan.

Nevertheless, Jason and Drew had a great time and went to a bar afterward to continue the date. By the time they left, the train had stopped running, which was Jason's plan for getting home. Drew, being the true gentleman that he is, drove Jason all the way out to the suburbs, which ended up being a 1.5-hour roundtrip journey just to save Jason from having to spend $$$ on an Uber. I guess he just really liked him!