Can I Date Someone For Their Money While Hooking With My Ex On The Side, If I’m Stealing Money From My Ex To Make Things Even?

Dear Doctor:
In troubled economic times like these, is it okay to date someone for their money while having sex with an ex-boyfriend on the side? To make things sort of even, I steal twenty bucks from my ex boyfriend every now and then.
Sincerely, Poor Gurl

Dr. Damage, who throws nickels around like manhole covers, sees your problem in chiefly economic, as opposed to romantic, terms. If the Doctor were Larry Summers, he’d say you are robbing Peter and robbing Paul, too. In this way, you’re a little like Bernie Madoff, but without polo ponies. But we digress. We see some hope here- by purloining only $20 per visit rather than your ex’s credit card or a c-note, we see restraint and, we dare say, responsibility in your actions. Plus, unless you’re not telling the whole truth, the fact that you are not making surreptitious withdrawals from your new boyfriend is cause for hope. Because, as the good Doctor learned in medical school (he paid attention in this class), it is really up to your boyfriend to make additional withdrawals, if you know what we mean.

As you note, these are hard economic times that require extraordinary measures. Some would suggest that you broaden your revenue-producing activities by involving yet another unwitting former boyfriend. But the Doctor would advise against this.

He has been in the unwitting seat before, and would not wish it upon any other males who are as dumb as he was as a young man. To fashion a plan to get back down to one boyfriend at a time, as this is the only sustainable arrangement going forward, the Doctor suggests that rather than spending the ill-gotten gains on things that you don’t really need, that you invest 50% of it in troubled assets and credit-default swaps which are risky (but not more so than having two relationships and stealing from one of the suckers), and the rest in bonds and T-bills. Naturally, as you approach retirement, you’d probably want to adjust those investment ratios, but if you’re sleeping w/ two men now, the Doctor surmises that you’re still a few years away from the dreaded AARP discounts.