Cliff is a grown adult seemingly depicted with an attraction toward teenage girls, and as a result, favors girl-only pop bands instead of boy bands, to the disagreement of Andee, and is occasionally heard masturbating on air to the thoughts of being in company of them. On one occasion, Cliff has voiced intentions to manage a new girl band dubbed "Lost Innocence", that would consist of teenage girls. Cliff has also claimed to have coached an all-girls softball team.
On the other hand, Cliff is apparently uninterested in older women, as seen when he lambastes Andee, who was 26 in 1998, for wearing a tank top at this age (Cliff favors a teenage co-host instead). Due to Andee's age, Cliff displays a lack of respect towards her, perceiving her as being nothing more than a minor staff who is meant to only "laugh at the jokes" and not "suck up" and try to get Cliff's job.