The more Harry interacted with Penelope Logan, the more determined he was to set her up with his best friend. The real question was how.
Roman had been more depressed than usual since his breakup and it wasn't even because he cared about Leslie. He worried that it was too late in his life to form a meaningful connection.
He didn't say it in so many words but it was fairly clear from the way he acted. After being friends for fifteen years, Harry could read him like a book.
Unlike him, Roman didn't enjoy meeting a whole bunch of new people. He was the loyal type but he had never found someone who made him feel anything real so things never ended up working out.
His parents had messed him up pretty good. Roman might not resent them for it but Harry did. He was indignant on his best friend's behalf. He would never forget the way Roman was when they first met.
Awkward. Way too overscheduled. Surprised that anyone wanted to be his friend.