QUESTION FROM A GREEK TRAGEDY READER: I’ve enjoyed your blog for years, and I’d love your opinion on an issue I’m having with a guy I’m dating. We are both in our mid 20’s in professional school. Even though I work summers, money can be a bit tight throughout the school year. My guy has loads of family money and is very generous. (I recognize this as a problem many women would love to have). My main issue is this: when do I assume he will pay? Often he will suggest tickets to games or restaurants that I cannot afford. I will generally say this and then he will get slightly irritated and tell me he was going to pay. I hate to have the same conversation over and over and OVER again, every time he suggests something fun. At the same time, a longer and more in depth conversation about it seems a bit awkward, especially since I will be able to afford these types of activities when we are done with our program. How should I stop feeling like a guilty free loader? 
Before I take a smack + crack at answering this (and I will), I’ll let others weigh in with their own words of wisdom. Floor’s all yours…
My advice, as promised (written prior to reading comments): The definition of a freeloader is a person who takes advantage of others’ generosity without giving anything in return. I don’t know you, but the fact that you’re even asking this question, at all, tells me, that ain’t you.
Since you’ve already voiced your "What a rockstar idea! I love it! But crapjacks, I can’t afford shite like that, loveass buns" I agree that a formal discussion drawing even more attention to your financial insecurities is a NO. So my advice is twofold:
ONE: Buy a sex book. Do nasty things. Initiate.
Easy feminazi’s. It’s not my go-to advice because of a sense of obligation, or for a way for you to prove your "worth" by making it "worth his while." I bring it up because I believe it will make you feel more powerful. Assertive. More aggressive. Less woebegone. I also think it will boost your confidence and remind you that your worth his time, his doting, his date planning. If you had the means, wouldn’t you just want him to appreciate it and have fun with you? Remember that.
TWO: I wouldn’t dare suggest love coupons.
I’d rather staple my lip to a wall. There is nothing sadder than a book of IOU’s, except perhaps, for air guitar. But planning a picnic date with him, where you do all the planning and surprise him, that’s reciprocation. Because it shows effort. No lengthy talks needed. Show don’t tell. Show him that you appreciate all he does by giving to him in ways you know. If that doesn’t work, go back to my first point, and get a pillow for your knees.
GOT QUESTIONS? NEED ADVICE? If you have questions or need advice on anything from where to eat to how to get over the bastard, just email your question to my advice email address. Nope, I’m not a shrink, but since people keep asking for my opinion, I might as well share it and air it, so everyone else can weigh in too.
