As Patron mentioned, is always smart to prepare for the worst, but you have a very small chance - minuscule really - of being interrogated when flying instead of driving. But your past posts lead me to believe you prefer the drive.
If it is any comfort, back in 2016/17, I flew up six months in a row. Literally. Not a single issue. Not one eyebrow raised in both directions. I used the “I’m going to the casino and trying to get a hockey ticket on stubhub”. I got nothing more than a “are you carrying any cash?” I usually delete my inappropriate texts, but it’s not illegal to call an escort service. Could customs make an issue after seeing escort texts? Sure. Will they? More than likely not. They’re looking for drugs, guns, trafficking and illegal business. Nobody is filling out paperwork because you want to see Candace at Euphoria unless there is something in your history to give them pause. Just don’t get caught in a lie. If they get access to deleted escort texts, tell them you had thought about taking a girl to a club or casino but all that fell through. Your buddy lied to you about how cheap it was for an evening. Too expensive, total ripoff.
My first drive into Canada solo was the only time I got 4 or 5 questions. I was naive about tight border security in friendly Canada so wasn’t anticipating any questions so I likely seemed annoyed. Coming back that trip I was asked to pop my trunk, and that took 10 seconds for a quick inspection. I’m sure I seemed annoyed again and likely did an eye roll. I know others have not been so lucky.
Just me....if you’re driving get a burner phone up there and ditch it on the way back. Not sure if that’s possible or practical for you, but you’ll have peace of mind. You would be okay I think doing nothing other than deleting texts.
Maybe I’ve watched too many crime series, maybe it’s white male privilege (kidding), maybe it’s overconfidence....but I never got nervous in those situations or give a second thought ...I just tell myself “these guys don’t give a flying fuck about someone like me”. Been right after dozens and dozens of trips.