| Hint | Answer |
| Has an older brother | |
| Has a younger sister | |
| From Ohio | |
| Is frequently called by girls' names | |
| Has a girl's middle name | |
| Hangs out on the roof of his apartment | |
| Hangs out on the roof of his workplace | |
| Owns a pair of red cowboy boots | |
| Owns a pair of red cowboy boots | |
| Dated a doctor played by Sarah Chalke | |
| Dated a doctor played by Sarah Chalke | |
| Shared an apartment with his best friend and best friend's wife | |
| Shared an apartment with his best friend and best friend's wife | |
| Subject of frequent jokes about his hair | |
| Subject of frequent jokes about his hair | |
| Has a best friend nicknamed 'Big Fudge' | |
| Has a best friend nicknamed 'Big Fudge' | |
| Has a best friend nicknamed 'Chocolate Bear' | |
| Has a best friend nicknamed 'Chocolate Bear' | |
| Has an older brother | |
| Has an older brother | |
| Has a younger sister | |
| Has a younger sister | |
| Rides a scooter named Sasha | |
| Rides a scooter named Sasha | |
| Best friends with his college roommate | |
| Best friends with his college roommate | |
| From Ohio | |
| From Ohio | |
| Has a girl's middle name | |
| Has a girl's middle name | |
| Is frequently called by girls' names | |
| Is frequently called by girls' names | |
| Hangs out on the roof of his apartment | |
| Hangs out on the roof of his apartment | |
| Hangs out on the roof of his workplace | |
| Hangs out on the roof of his workplace | |