Lien on me
My 31-year-old boyfriend has the best clothes, cars, electronics, takes me to the nicest restaurants ... you get the picture. He told me he was "an investor," working for himself, making online investments. I eventually asked how he could afford his lifestyle in this economy. He said he "comes from money," and has a trust fund. To me, the fact that his father's a doctor only confirmed there was family money. After six months, he took me to meet his parents. I assumed we'd pull up to a mansion, but it was an apartment complex reminiscent of college housing! I'm not materialistic. I'm from a blue-collar family and have worked since I was 15 (I'm 27). But after a year together, I'm wondering whether he's a liar with tons of debt. Asking questions is hard because I don't want him to think it's the money I care about. I love him and believe he may be "the one," but may rethink that if he's carrying a million in debt. — Worried
If you don't get to the bottom of this, little things you take for granted — like being able to afford the bologna portion of your bologna sandwich — could become a really big deal. Suddenly, "grabbing something at the store" means running out fast enough to elude the fat security guard.
You're way overdue for figuring out whether this man and his means are living apart — probably because you're kinda jazzed by all the things money can buy, and feel guilty because of it. Sure, if this guy is on the level, just by being with him, you could eat daily at a fine restaurant, and not because management is nice enough to feed you before your shift.
Keep in mind, you weren't looking down the bar with tiny binoculars to see which guy whipped out a platinum card. You're a hardworking girl who fell for an "investor" with no apparent means of support — unless you count his daddy, supposedly a doctor with piles of money who's living like he just completed his residency to be a lawn doctor.
Your boyfriend may have a trust fund of sorts ("Trust me, Pops, this is the last time you'll have to bail me out"). Even if he has a permanent pipeline to serious family money, can you really respect a 31-year-old man who's still living off Mommy and Daddy? After all, it's not like he's doing it to bring clean water to poor villagers in Africa.
I'd guess that he's day-trading, a profession that works for many like that old joke about how to make a small fortune in aviation (start with a big one). Unfortunately, it's human nature to keep believing that your big score is just around the corner — the corner you hurry your girlfriend by when you're trying to pass off the repo man as a valet with a tow truck.
Appearances can be deceiving — especially to girls too needy for love and fearful of disapproval to say "Yoohoo, what's that red flag over there?" Early on, you get information by giving it: talking about how you grew up and how you see money, and drawing his background and values out of him. You look for incongruities (especially outrageous ones) and ask about them until you get satisfactory answers. That's what you need to do now — after laying out your feelings for him and your fears. If he explodes or just stonewalls, the truth is probably what you suspect: A fool and his lines of credit are soon parted, and sure, you'll be able to take your kids to the dentist — as soon as you find a buyer for your left kidney.
Seconds on carats
You gave bad advice, telling that poor girl to return her engagement ring to the fiancé who broke up with her. The ring was his mother's. Well, this girl's the dumpee, so that ring is now hers. My advice? Sell it to finance a fabulous vacation with her girlfriends. — Know Better
If you're from a country where your daddy won't get the same number of goats if you've done the impure act, then sure, when a groom-to-be hightails it, some bling should change hands. But here, the whole ring thing is weird to me. If men and women are equals, how come the guy has to give the girl an engagement ring but nobody expects her to buy him engagement golf clubs or an engagement boat? Even weirder is the impulse to hang on to the ring after the engagement is kaput. It's a failed relationship, not a failed revenge plot. Acting vindictively says you weren't so much in love as you were desperate to be loved. You are what you do, and there's a high road to take here — and it doesn't lead to Benny's Pawn Shop.