What’s interesting is that once you’ve engaged in these fundamental parent-conversations you won’t be accidentally unconsciously attracting/socially relating with men addicted to helping/enabling women. Notice that he intuitively (albeit unconsciously) 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 non-verbally as you do) “I feel a little insulted.” We know something's amiss because you don't feel good with his generosity and, we wonder if he would repeatedly pay for a young man's meal.

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 concept that probably would evoke denial. i.e.  “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.” No. They would think that you're unwilling to take care of yourself, to pay your own way; more likely they'd probably think you're, at best, a con. Most would agree that a woman who could take care of herself wouldn’t let him manipulate her. The first experience of successfully insisting is transformational, one is never the same thereafter.

You’ve also revealed a misunderstanding about responsibility; you’ve told your story from victim instead of from cause. i.e. "It just "happens," as opposed to, "I set him up to pay". An actualized women knows what’s right and fair and as such automatically causes a balance of energy exchanges. She knows from childhood experiences of having run all the cons during teen-dating (of not feeling wholesome/complete afterwards) and now operates from choice.

You’re lucky to be catching this behavior now, many ex wives now regret their teenage cons of setting it up for each new date to pay (possibly never having paid for any date). The anger it creates in some men (compounded with each instance) is awesome; during the divorce settlement process a man doesn’t know why he is driven to unfairly punish, to exact payment. Neither can he see that his integrity has set it up for him to be punished (in his mind, unfairly) for using women. Part of it comes from unconsciously setting it up to be used throughout his teens. An actualized boy, one who has a complete relationship with his parents, intuitively knows to date girls who get good grades, are involved in several school activities, and perhaps even have a part-time job, as such, they always include the words "Dutch Treat" in their invitations; girls are held to be equally capable. Boys who are not self assured are usually 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, one who can pay her way. In truth they fear that no actualized girl would go out with him because he’s too controlling and invariably dragging around too much anger. As 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 sense it does in fact represent something else (a debt being repaid, or a down payment, for something of greater value). Even if it's a gift, a deserved 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 you to fully comprehend the worth of his gift.  In fact, 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.   

BTW: It is possible to receive "gifts" from someone who's well off financially, but an exchange of equal/similar value must be arranged and insisted upon by the recipient and verbally agreed upon. If the giver won't let you even take them on a picnic then you're hanging around an enabler; in this case, it would be the giver (your friend) who possibly can't get a date with a social peer and so he opts for someone he can impress and control. He might simply be assuaging his ego or getting peer-points for being seen with an attractive woman.

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 are "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. All spouse abuse begins with such early unconscious biases.

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, for you 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). My sense tells me he will have no choice but to argue, defend, and justify his behaviors. A conscious man would reply, "Thank you for sharing all that. I get it.  It's a perfect wake-up call for me."

Readers who recognize themselves can determine the approximate debt (over their lifetime) and pledge gifts/time to a charity so as to create an experience of integrity, so as to preclude the consequences of using.

Great letter. Many will see themselves. Aloha, Gabby

P.S. Please do not misconstrue my reply to imply that he is not a nice and generous person and a friend worth having. It's simply that you're both stuck in teen dating behaviors.

* 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).

Check back occasionally for minor edits (last edited 11/28/11)