Working with a financial advisor isn't easy for many people. It's a special strain for those who, like myself, are at ease brutalizing disembodied customer-service reps over the phone, but who tend to cave in when face to face with a pro wielding lots of big money words, like "investment," "long term," and "balanced portfolio."

Which is why many of us end up taking advice from friends and relatives. The problem there, of course, is that if you think that a stranger could care not a whit for your welfare, take a look at those closest to you.

As a cautionary tale, I offer the following record of my recent email correspondence with my brother-in-law, the alleged Wharton grad to whom I entrusted our kids' college accounts. As I look back, I'm reminded of the Tijuana hotel called The Hiltin, and I wonder if Robbie might actually have graduated from Whartin.

Sept. 14
Me: Hi, Robbie. Have you had a chance to look over the numbers I sent last week re: the 529 college savings plans? We'd really like to get moving now that Jenny's headed for middle school. Time flies! Speak to you soon. How's Deb?

Robbie: Note? Haven't seen it. How's Joanie? She must be in high school by now! Hey! You should think about college! Have you considered 529s? I have lots of info on them!!

Sept. 17
Me: You didn't get my message?

Robbie: Thaks for writing! But I'm out of the office and offline until the 26th. I'll return the message then. Thaks for writing!

Me: OK. Speak to you then. Try Spellcheck once in a while. :-)

Robbie: Thaks for writing! But I'm out of the office and offline until the 26th. I'll return the message then. Thaks for writing!

Sept. 26
Robbie: Been out of town. Just checking emails now. 177 unread! I'm drowning! Hey, I've got a great idea now that Jamie's "getting on in years": 529s. I'm sending an attachment, including a 1.2 million gigabyte PowerPoint file the marketing folks just came out with. Take a look, let me know, and we'll work up some numbers.

Me: I thought we went over the numbers about three weeks ago. Didn't you get my message?! We're getting kind of anxious about this.

Robbie: Message? When? What time? I thought we circled back on that already???

Me: No, I don't think we circled back.

Robbie: I sent a plan over a few days ago. Go back to last Tuesday -- that was, what, the 23rd? Between 3 or 4 and 6 p.m., I think it was. Take a look. Reread your earlier note to me and THEN my follow-up. Print them out. It's easier to follow w/ hard copies.

Me: Last Tuesday?

Robbie: Wait! My computer clock is an hour off, so it was probably between 2 and 3 and 5 at the latest. P.M. What time zone are you in?

Sept. 29
Me: Whatever. So, where do we stand on the 529s?

Robbie: Stand? Right now I'm knee-deep in it, is where I'm standing. Whew! What a week! Anyway, as to time, I'm in Central Standard. So that's what -- an hour behind you? Or is that ahead? Didn't we have daylite savings? So that would be 3 o'clock to you? Or to me? But if my clock is off, then it's probably -- is it ahead or behind? You gotta be an engineer to figure this stuff out.

Me: College, Robbie. I don't mean to press or be rude, but we really need to square this away. Can you help us with college? I feel we're missing opportunity and time. I'm very anxious and I'd like to get it settled.

Robbie: Good point. I agree. Hey! Check out Holy canoli!!! But don't tell Sharon! She's still my kid sister, you know!! What's going on w/ college??? You better get on the stick, pal. Harvard ain't getting any cheaper!

Sept. 30
Me: I just called Wharton. They never heard of you. You're fired.

Robbie: Hey Sharon, what's with your jerk husband? Where does he come off treating family like that?! What a jerk. How's Jemma? You guys better start thinking about college. Let's talk!

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Rich "Snake" Pliskin is a humor writer who lives in Princeton, N.J. He can be reached at