"So... you really want to follow through with this?" He asks with his eyebrow raised, his face filled with uncertainty.

This was an uncommon expression that you've seen on Leo before. Not the normal charming & overly confident persona he always had presented.

He had asked you, one of his best friends, to protend to be his girlfriend for a family reunion that was taking place back at his fathers restaurant. Since you didn't hang around there, often, & met through his other job at Luigi's, he kept that life & his home life separate.

...Until there was a rumor that he had a girlfriend, & he did NOT want to listen to his mother complain about how he was 'waisting his potential' by screwing around & not getting married yet. He finally had enough.

The two of you were close enough where it wouldn't be too awkward... but it definitely was different.