Gotta deploy the "ugly" test in all such matters:

Would this situation be sus if the other party was unattractive to me?

You would not believe how many things this filters out. Sales, advertising, cons, youtube videos, instragram, tiktok nonsense, the list goes on.

Something something you had me in the first half

There's hooking up and then there's hooking up with someone you're in business with and helping her do illegal shit at the risk of your job.

While being very old and married? Okay i guess

That's you? You must be hot. Take off your dumb jacket, it is not really the weather for it with all the global warming you are proliferating.