He won and lost some money

We need a money category.

OK, so I'm at the very beginning of a relationship with a wonderful, caring, thoughtful, even-tempered guy. There's a bit of an age difference (he's 9 years younger) and a few other minor social differences, but variety is the spice of life, right? We click wonderfully. Even though it's early (and when I say early, I mean there has been no exchange of "I love you"s yet), he has been very forthright in sharing difficult information. So what's the problem?

When he was in his 20s he hit the lottery for a significant amount of money (in the neighborhood of $2 million). Being young, dumb, and single, he managed to squander it away like a wayward rap star over the course of five or six years, taking what should have been 20 years worth of payouts in advance and "selling them off" for the cash. The one "real" investment he made into a business venture collapsed.

While all this shows a lack of judgment mixed with a little bit of horrible luck, he's managed to right the ship, learn from his mistakes, and move on with life over the past eight to 10 years. Except -- all of those "advance payments" he took? There was no tax withheld on those. So he currently owes the IRS an amount akin to the value of a modest home in a Boston suburb.

My question to you (and your readers): Since the relationship itself is currently 100% enjoyable and wonderful, and he displays what I seek in a mate, should I just stick with the status quo and enjoy what we have and see how it plays out? Or would you turn tail and run away from an otherwise fruitful relationship with this giant financial guillotine hanging over your head?

– What Am I Getting Myself Into?, Beverly

Wow, WAIGMI. I mean, there's no right or wrong here. This is about what's in your gut.
Can you commit to a guy who will probably be making hefty monthly payments to the IRS for the next few decades? Would it be any different if he had to make the same monthly payments for child support? Or to help a sick relative?

My guess is that this has less to do with the guillotine and more to do with what the stigma and the what-ifs. Are you concerned that he doesn't have a good plan for paying the IRS? Do you fear that he'll make financially irresponsible decisions in the future? If you can say "no" to those questions, I wouldn't worry about the stigma of the financial loss. But if you're worried that he'll make poor choices again or behave impulsively because he's almost a decade younger and terrible with money, well, talk to him. And then be honest with yourself.

"Since the relationship itself is currently100% enjoyable and wonderful, and he displays what I seek in a mate …" I mean, that sounds pretty great. If you feel secure that his past is in the past (despite the leftover bills), I would just focus on the present and consider what he owes to be his "baggage" -- just like any other life experience.

He is who he is because of what he has been through. If he had invested that $2 million like a pro, maybe he wouldn't be so enjoyable and wonderful.

Readers? Would you date someone who owed hundreds of thousands to the IRS? Is the age difference an issue? What's going on here? Discuss.

– Meredith