What to Do When a Woman Is Demanding Before the First Date

You have two good options, and our coaches would pick between them by asking what you want from her. You can answer lightly, tease her about being demanding, and take her somewhere inexpensive where paying for drinks costs you little. Or, if her demand has put you off, you can drop her. Both are fine. What you should not do is argue about it, comply with a long list of conditions or plan an expensive evening to prove yourself. A student asked us this on a live call after a girl told the student she would go out only if they did all the planning and paying, and that was the shape of the answer.

The coach's first question was whether this girl was a hookup or a long-term candidate. That changes how much the demand matters.

If you mostly want to see her and see what happens, you can go along with the plan and keep it cheap. Her demand does not damage that outcome much. If you are looking for a girlfriend and the demand turns you off, it has told you something about her. In that case the coach's view was that she has disqualified herself, and you do not need to go.

The coach also pointed out that you can always date a girl like this and simply not spend much. Nobody gets used for money unless they are willing to be a mark to some extent. A woman cannot take advantage of what you never offer.

The coach said that if the point is mostly to see her, the answer is to agree to make the plans and pay, and then pick a modest place. Drinks at a moderately middle tier bar, not a dinner. Pay for the drinks happily and treat it as a small risk: if the evening goes well, great, and if not, he did not spend much.

Then answer her with humor, not a complaint. The coach's examples were along the lines of "I see you are quite demanding, but I can handle that for a first date," or "That is a little upfront, but fair enough." You can also add that since she is coming out to meet you, you do not mind paying. That reads as you being generous, not as you being told what to do.

Keep it light. A smile is the difference between "you are a bit much" as a joke and the same words as an attack.

The other route is to end it. The coach said plainly that you are allowed to cut a girl off whenever you do not like her or do not see possibilities with her. If a demand before you have even met has put you off, you can thank her, say it does not sound like a fit, and go back to other plans.

There is no need to explain at length or to win the argument. A short, polite message is enough.

A related case came up on another call: a girl wanted flowers and the full treatment after only two dates. The coach's frame is useful here. You love doing nice things for a girl, but you do not like it when they are demanded.

The example was flowers. If you surprise her with a bouquet, it is a lovely moment. If she demands one, it takes all the fun out of it, and nobody enjoys it, including her. That is a reason, not a rule, and you can say it with a smile.

Other small moves from the same answer:

• If she asks for something in a demanding way, answer the way you would tell a child to mind their manners, and make her say please.
• You can joke about the list. For example, tell her you also need a promotion, a massage and silk slippers, but you are not getting those either right now.
• Play it down. Make it sound a little silly, not like you are cheap or unwilling to do nice things.
• If she does not demand, go ahead and do something nice she did not ask for. The nice thing lands better as a gift than as a payment.

Do not give a long speech about how you are not a wallet. Do not agree to a dinner you would be annoyed to pay for. Do not try to win her over with a bigger plan after she has set conditions. And do not stay in it if every message from her adds another demand.

If she is respectful of a small, relaxed first meeting, you can continue. If she is not, the same coach answer applies: the worst that happens is that you go on a date, find out she is not for you, and politely leave. That is not something to be afraid of.