When do you tell a date you owe a ton of money?

Wayne and Wanda

Dear Wanda and Wayne,

I read your response to the letter about the guy pretending to have more money than he does. You took him to task for not being forthright at the outset about his financial situation. I'm in a similar situation, not that I'm pretending to be rich. I owe a lot of money. Being honest about it scares people away.

If I bring it up right away, the person I'm interested in thinks that I'm already thinking long-term. It's a lose-lose either way. When do you think would be the best time to bring up my debt situation? It's already stressful enough, and it's embarrassing to talk about.


-- Mr. Moneyless Bags


Wanda: Personal finance isn't a first-date topic, but it can influence a courtship. Obviously if you're cash-strapped, that can temper butterfly-fueled urges to trend indulgent and go big on those first dates. And that is your first opening into the tricky topic of finances: Tell your love interest you're watching your spending and you're on a budget. There's plenty of non-expensive fun to be had anyway, and you hope she's on the same page.

Her reaction to that will give you a preliminary read on whether you can agree. If the relationship progresses, and if and when the relationship takes a more serious turn, have a frank chat about your challenges and emphasize your commitment to resolving them. Tell her you aren't informing her because you're ready for joint bank account status, but because you respect the complications of personal finance and you want to be clear about your situation.


Wayne: It's tough enough being a baller on a budget, but then you add in having to wow your love interest and prove to them that you can provide fun (and potentially for a family)? Hello stress! But take it from this fiscally responsible Romeo -- you don't have to be Daddy Warbucks to be a Mack Daddy these days.

Get online and start saving! Like, follow and friend all the local and nearby restaurants and entertainment options you can and subscribe to their mailing lists. Sign up for Groupon and other popular digital deals. When you plan to shop for dating treats and gifts, do a Google search for retail coupons.

Look at you -- saving money and saving your dating rep! Oh, and one more thing to save: the bank account and debt convo for down the road. Until you're serious, keep that in your back pocket with your nearly empty wallet.



Wayne and Wanda weren't alone in their cautionary approach.

Frequent sage commentator Moniquesmom cautioned the original letter-writer to "look out for No. 1." She made an excellent point when adding that "the fact that his parents had to drop his butt and let him fend for himself should be a warning sign for you, my dear. Don't ignore the signs." She suggested our writer let her partner "get himself together first then maybe date him." If the relationship was going to go on, the commenter suggested economical dates -- like cooking dinner together at home.

Another commenter, Corkyb, warned this relationship had "trouble" written all over it. After some choice reprimanding words for Wayne, he gave kudos to our lady for considering her future. He argued the woman's man "HAD to confess" -- and that he didn't do so to come clean but because he was out of all other options. "Remember," Corkyb said, "his own parents have written him off."


Wanda: An excellent takeaway from both these readers -- this guy's parents cut him off. Assuming they have normal, loving parental sensibilities, that is a pretty big deal and perhaps speaks to their level of frustration with their son's behaviors. Is this alone enough reason to dump a dude you've spent a year with? I say no, but it's a wide open door into a deep discussion into how things got to this point and what he plans to do about it.


Wayne: Unlike this week's letter writer who is just trying to set a solid foundation while saving a few bucks, the previous broke dude was living a lie and breaking his partner's trust. I'm still confident there were warning signs along the way, but I can't say that for sure and, as they say, love can be blind. Especially when there are diamonds and champagne sparkling everywhere!

• Wanda is a wise person who has loved, lost and believes in retail therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at wanda@adn.com.