Ask Amy: Generous man was played for a pinata

Dear Amy: I have been on a series of dates with an established professional. I got the feeling that she just viewed me as a money piñata, even though I imagine she out-earns me.

We are both late-millennials. We established values of equality, reciprocity, family, etc., before we even met in person.

We had a great time on our first date. The bill arrived and there was no casual dance back and forth over who might pay. She never even looked in its direction. No worries, I got it.

Second date, we also had a good time. The bill arrived. Same thing. This time I let it sit on the table for probably 15 minutes before I placed my card in the folder.

We decided to meet again.

This time, she asked if I would like to split the bill with her.

This behavior confused me. I called her out by asking, “Are we on a date, or are we friends meeting for dinner?” She insisted we were on a date.

I said, “Well this is intriguing, you want to go Dutch on the third date, but not the first or second? Her reply was a cool: "Yeah.”

Wanting to leave without creating a conflict, I simply paid the bill and expected not to speak to her again.

The following week, she invited me to brunch.

Everything went fine but, hey, now I’m curious about what is going to happen when the check arrives.

Sure enough, she doesn't even look at it. I let it sit on the table for 30 minutes before the waiter returned wanting to cash it out.

I paid the bill and thanked her for inviting me out … to pay for her meal.

She looked confused, as if I had broken some unspoken rule of dating in which the man must pick up every check.

I have been rejecting her calls and texts to "get together" ever since.

I'm curious about what you think of this.

— Would Like Equality

Dear Equality: I am 100 percent on your side. But I have to ask: If you’ve been played so many times, then why have you kept throwing down your card?

Granted, your mutual staring contests when the check comes are amusing, but you’ve been outflanked.

When two people connect online and mutually agree to meet, they should split the check. After that, when one person asks the other out, they should also offer to pay the bill.

In the future, a conversation might have avoided this gamesmanship. You took a baby step by asking whether you were on a date or a friend-date, but you never followed up by sharing your own views or describing how her behavior made you feel.

I’ll fill you in on what the kids are doing these days. They use Venmo or PayPal to basically bill their dinner partners after the fact, if they believe they are owed money.

Dear Amy: I am responding to “Sexless at Sixty,” a woman who was worried about her husband’s libido. She said she always had to initiate sex.

I am a 94-year-young gentleman. I have been alone for nearly three years.

I now have TWO lady friends, both sexually active, as am I.

I see each of them at least once a week.

Fortunately, they live about 40 miles apart, and do not know each other.

Tell the ladies that it is OK for them to initiate the "action.”

It's time for them to understand that being aggressive is modern, and it is OK with us.

— Happy Man

Dear Happy: I wonder if your two lady-friends would mind the fact that you are sleeping around; if not, you’re good, but you should make sure that each woman knows that you are not sexually exclusive.

It is also VITAL that you and all of your partners get screened for STDs.

Dear Amy: I had an additional thought regarding your excellent advice to “Sexless at Sixty.” It appears that the absence of sex in the writer's otherwise solid relationship with her husband is largely, if not entirely, due to an absence of desire on his part.

I suggest the husband might discuss this with his physician because there are a number of physical issues that should be considered as the cause of his absent libido.

Side effects of medications such as antidepressants, low testosterone level, other easily corrected culprits should be considered.

Clark Chipman, MD

Dear Dr. Chipman: Absolutely! Many respondents have noted that their own sexual dysfunction was reversed after seeking medical advice.

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(You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)