Gallantly paying for dinner is an admirable gesture. However, your irritation indicates that you need to balance your generosity with a little self-preservation.
There are plenty of people who would happily order the best wines at dinner and then allow you to pay for them. Paying for people who repeatedly take advantage of you may result in resentment and financial stress.
Ask yourself whether you have a sense that your mere presence is not adequate in itself and that you need to do something extra to be acknowledged and appreciated. When the desire to be appreciated becomes excessive, it becomes self-defeating. You attract those who will take advantage of you, and the gratitude you seek will never be satisfying.
So unless you’re independently wealthy and enjoy playing to a stream of pandering free-loaders, you may benefit in toning down your magnanimity.
If you go out with people who tend to feel entitled, simply bring cash and only pay your share of the check, plus extra for the tip they may conveniently forget—or ask for a separate check at the beginning of the meal. More importantly, remind yourself that your presence alone is sufficiently valuable.
by Alison Poulsen, PhD