Bennett co-starred in the 2004 comedy movie Mean Girls as Aaron Samuels, the love interest of star Lindsay Lohan's character.

In 2009, he starred as the title character in Van Wilder: Freshman Year,[9] and appeared as Nick in the Hallmark original movie Elevator Girl.

[14] In 2019, he was featured in the filmed poem rendition Love Goes Never Alone, in support of the LGBT+ community, for the online theatre publication First Night Magazine, performing next to other film, television and theatre celebrities such as Stephen Fry, Alan Menken, Stephen Schwartz, Debra Messing, Neil Gaiman, and Sharon Osbourne.

[16][17] In 2021, Bennet played Jesus Christ - as an imaginary best friend to the eponymous Russian boy in Wes Hurley's Potato Dreams of America.

In 2024, Bennett was announced as the host and the main judge of Hallmark's reality series Finding Mr. Christmas, which premiered on October 31, 2024.

[20] On November 30, 2020, representatives for Bennett confirmed he was engaged to Amazing Race contestant and current Celebrity Page host Jaymes Vaughan, who proposed on the set for The Christmas House with an original song.