|Relationship|| Tricia (broken up)|
Caitlin (broken up)
|First Appearance||Sweet 6teen|
|Last Appearance||Baby, You Stink|
In Sweet 6teen, Benj was first mentioned by Caitlin as an object of her affections. Caitlin tried to get him to ask her to her sweet sixteen, and was making progress until she learned that Tricia also wanted him. After hearing about this, Caitlin suggested that they hold a fair competition for his affections, with whichever girl he asked out first getting to date him. Needless to say, Tricia cheated, first interrupting the two when Benj was about to ask Caitlin out, and then when Benj asked if Caitlin was into him, outright lying and saying that she wasn't. Instead, Tricia suggested that he ask her to her sweet sixteen, which Benj agreed to do.
Soon after asking her, Benj learned that she was shallow and cruel. His first inkling of this was when she acted like a spoiled brat to the workers erecting her massive party, but this was confirmed later in the episode as he saw her being incredibly rude and mean. He ended up leaving her for Caitlin, and along the way pointed out that her actions were captured on tape by the Chill TV crew. He ended up dancing with Caitlin on the ice rink, and the two started going out.
Baby, You Stink
After two dates, Caitlin took Benj to a "baby-making" booth that had been set up in the mall. (This was a booth that took photos of a couple and spit out a picture of what their future baby might look like.) When they went inside, things went badly, as the two were incapable of making a good-looking baby. This caused Caitlin to break up with Benj.
- Benj was the first guy Caitlin dated in Season 3.
- Benj is the second guy Caitlin has competed with Tricia for. In "Unhappy Anniversary", she competed with Tricia over Zane (although that case was more Tricia not wanting Zane to date anyone but her after he dumped her).