The biggest challenge for the over 50 group is that many have been in long-term relationships and haven't dated for years; they need to learn how to date all over again. It's a terrifying prospect for them to get naked and intimate with someone new.
Bring your phone so that you can smartly map out where you and your date are meeting, so you can get there nice and early. If you are going to a place that doesn't take reservations, arriving well before your date will ensure you're not awkwardly huddling in the freezing doorway, waiting for a table to open up.
Men may take women out on different sorts of dates than they previously did, but the expectation that men be the ones to do this largely remains. When it comes to dating, many men are expected to pay for dates, both by some women, and more commonly, by themselves. Men paying for women on dates because they enjoy their company, and view it as a kind gesture, is not an issue. The issue is that some men still pay for women simply because they are women, and the men would feel emasculated if they did not.