Hold Me, Tightwad

Advice Goddess: Aug. 11

My boyfriend moved in with me after his landlord raised his rent. He announced that he’d give me $400 a month (half of what he was paying at his place), then cut that to $350. I pay $1,250 a month for my home loan and utilities and more for groceries, lawn care, etc. Now he’s decided he shouldn’t have to pay anything because he never charged me when I stayed over frequently at his apartment one year. He occasionally buys groceries, takes me out to dinner monthly and had a little remodeling done ($1,200). He also bought a freezer ($400) and a side of beef ($1,000). I love the guy. He’s lots of fun, sex is great and he only started being this way when he learned that I was helping my sons out with about $60 a month. (Both just graduated with extensive student loans.) He said he was never helped like this by his parents, and apparently money’s no problem for me if I do this.
— Disturbed

There’s a time in a man’s life when he shouldn’t expect to contribute to keeping a roof over his head, and it’s when he’s waking up on sheets with little cartoon spaceships on them to go to his day job — attending fourth grade.
What kind of disturbed cheapskate tells his girlfriend she’s lucky he didn’t charge her for rent, gas and electric on all those nights she didn’t drag herself out of his bed and drive home immediately after sex? But, wait — it gets better. He’s so petty that he justifies his freeloading by pointing to where some of your money’s going — to help your just-graduated kids out in a tough economy. (Some ladies have meth habits; it seems you have a nasty mothering habit.) And not that it’s any of his business, but wow, $60 a month? Why, with that kind of loot, your boys’ll be able to go in on a 2011 Jag — in another 1,166 years.
Nothing says “We’re in it together, babe” like a man telling a woman she’ll be covering all the bills. OK, so he was never helped out financially by his parents. We all have some point in our lives when Mommy didn’t give us a cookie. If it affects us long-term, the correct thing to do is work it out at Mr. Therapist’s office, not make it part of an elaborate rationale to stiff the girlfriend on living expenses. Sure, he contributes in some ways ($1,400 of frozen beef), maybe because he likes steak and maybe because he feels guilty for being a mooch, but your mortgage documents surely don’t allow you to pay with cash, check or cow.
It shouldn’t be hard to get him to start contributing. Just hold him by the ankles and shake all the change out of his pockets. What you can’t cure is the character flaw that leads him to show all the generosity of spirit of an angry accounts receivable clerk. Of course, it takes two to make the sponge dynamic work — one to do the squeezing and one to ignore being squeezed. Ask yourself whether you need a relationship — any relationship — so badly that you’ll settle for parasite/hostess. That’s what you’ll keep settling for as long as you stay focused on the positives here, like how two can live as cheaply as one when one’s stiffing the other on the rent money, and how he’s so much fun and sex is so great. (It had better be. You’re paying $625 a month for it.)

Too Mosh Information

I have tickets to a rock concert next week. I’m interested in a woman who works at my regular morning coffee shop. How do I ask her to dinner and the concert as a first date without it seeming like a consolation prize (like she was my last choice at this late date)?
— Hopeful

The issue isn’t the late date, but inviting a woman you barely know on a romance-soaked date-athalon, which is what it becomes when you add dinner to the equation. (Think hostage situation with linguini and roving violinists.)
The concert invite alone is a bit much, with the ticket price, two or three hours at the event and a couple hours getting in and out of the parking lot, but it allows for plausible deniability on the romantic nature of your intentions. If she’s not into you, she can play it like you just had an extra seat, and you can tell yourself she just wasn’t into Bowels of Satan or whomever and go back to your normal coffee provider/providee relationship.
Ideally, though, you’d just invite her out for a drink, which would tell her what your intentions are, but without going straight from “Double latte, no foam” to “I’d like you to be my breed sow.”