Hi Young But: Many readers are wincing at your feigned ignorance and for being stuck in victim. You have some understandings about the problems inherent in sexism but not enough to know better.

You letter reveals that you've yet to have one of thousands of conversations* with your parents, during which all this is communicated (when something is communicated it is gotten —it is known—as opposed to understood.)

What’s interesting is that once you’ve engaged in these fundamental conversations you won’t be accidentally unconsciously attracting/socially relating with men addicted to helping/enabling women. Notice that he intuitively knows that you can’t be trusted to say what’s on your mind. Respect is missing. You wear your fear on your face, to men it’s an aura thing. An actualized woman would tell him, verbally (not nonverbally as you do) “I feel a little insulted.”

BTW: "I feel a little insulted" is a make-wrong. It would be easier for him to get if you shared, “I’m uncomfortable,” an experience as opposed to an arguable/deniable concept, that probably would evoke denial, “I didn’t mean to insult you.” or, "If I insulted you I'm sorry." The word if is a covert denial, a sneaky make-wrong.

Re: “…someone would think I’m unable to take care of myself.” That someone (regarding this issue) would be correct. Most would agree that a woman who could take care of herself wouldn’t let him manipulate her.

You’ve also revealed a misunderstanding about responsibility, such that you’ve told your story from victim instead of from cause. An actualized women knows what’s right and fair and as such automatically causes a balance of expenditures. She knows from childhood experiences of having run all the cons and now operates from choice.

You’re lucky to be catching this behavior now, many ex wives now regret their teenage con of setting it up for the boy to pay. The anger (compounded with each instance) it creates in men is awesome; during a divorce a man doesn’t know why he is driven to unfairly punish, to exact payment. An actualized boy, one who has a complete relationship with his parents, intuitively knows who to ask out—girls who get good grades, are involved in several school activities, and perhaps even have a part-time job, so that they can select their Dutch treat dates. Boys who are not self assured are attracted to girls from a different (seemingly lower) economic/social group because they simply don’t know how to get into communication with an actualized girl, a social peer. In truth they know that none would go out with him because he’s too controlling and invariably dragging around too much anger. It‘s a matter of control—paying for the first, and subsequent dates creates possible debt (favors owed.)

You’re running some unconscious lies that are not becoming; “and before I know it,….” Can you now sense some readers grimacing? And, “I appreciate the gesture.” I don’t get this. I don’t see it as a gesture, unless you experience it to represent something else (a debt being repaid, or a down payment, for something of greater value). It’s a gift. A gift calls for a sincere appreciative acknowledgment, a "Thank you!" I don’t get that you’ve paid an equal amount of money on boys and men throughout your life for there to be comprehension of its worth. Many reading this  suspect that there’s more behind his generosity. Your task is to remove all doubt from everyone’s mind; a somewhat equal amount of money spent by the both of you would allow everyone to feel a bit better about you.   

BTW: It is possible to receive "gifts" from someone well off financially, but an exchange of equal value must be arranged and insisted upon by the recipient and verbally agreed upon. If the giver won't let you take them on a picnic then you're hanging around an enabler; in this case, it would be the giver who can't get a date with a social peer and so they opt for someone they can impress and control.

Re: “I have told him.” What you’ve been taught by parents and teachers is how to talk. Now’s the time to start studying communication. When something is communicated it’s gotten. There’s no misunderstanding. There’s no doubt that No means No. Telling him and not intending it is a con. Wanting something is different than intending it. Partners who are in communication with each other acknowledge through-to-mutual-satisfaction any communication they experience as unconscious condescension or invalidation. His you're "young..." retort is both condescending and an invalidation of your experience. Not meaning what you say is a lie. Even unconscious lies have consequences. Not recognizing his abuse and nipping it in the bud is your far greater problem.

Your question, “Is there something I can do to assuage my conscience,...?” is quite revealing. No matter what your mind might now think you meant, it communicates that you’d like to find a way to continue to have him pay your way, and, to feel good about it. My reply is in support of you committing yourself to communication mastery, of identifying the childhood incidents (referred to as incompletes), that set in the fear. There is a way of communicating, a communication model, that supports transformation, so that you are healthfully and appropriately assertive and attract mature men.

To feel good, to restore your experience of integrity, it would work for you to share this reply with him and acknowledge your unconscious con, and, arrange for repayment of some kind (so that your unconscious ignorance isn't rewarded.) Readers who recognize themselves can determine the approximate debt (over their life time) and pledge payments to a charity so as to create an experience of integrity.

Great letter. Many will see themselves. Aloha, Gabby

* It’s possible to have these conversations with a communication coach. The coach will support you in completing your relationship with your parents (this means either verbally cleaning up the incompletes with each or recessing them from your life until they get therapy).