Why You Shouldn't Play Money Detective on a First Date

I recently had a coaching conversation with a client about her "must-have's and non-negotiables" in a partner. We discussed her deal-breakers at length -- emotional, financial/career, intellectual, physical, sexual, and spiritual. I often advocate that single men and women "Be the dream partner you want to attract" so that whatever expectations and preferences you're setting up for someone else, you're being, doing, and living yourself!


She had some pretty high standards around ambition and earning power for her ideal guy.


Certainly, I've never met a woman who said, "You know, I'd really like to match up with someone kind of lazy and slothful..." (lol) And it's fine to desire a guy who has something going on in his life -- especially if you're kickin' ass and makin' bank in your own career as well! But be careful that this aspiration for upward-mobility doesn't drive the first-date conversation (or pre-date conversation). You could easily be perceived (or misperceived) as superficial or purely money-motivated.


Jut as men often screen women for youth and beauty, women sometimes screen men for wealth – or the potential to earn it. I'm not saying you should hitch your wagon to a guy who's perpetually unemployed and couch-surfing amongst his friends. But don't let financial screening create a handicap either. An affluent man usually wants to be valued and appreciated for ALL of the things that make him unique and special (unless he's financially secure but emotionally insecure -- different deal entirely!)


A high value woman can attract a high value man by prioritizing the discovery of internal values (this is done through vulnerable, intimacy-building conversation) and then, once internal value has been mutually demonstrated, having some honest money conversations


A different client complained that she'd been talking to a man for half a year and had no idea what he did for work, if anything. He was dodgy and evasive in his answers about how he spent his day or what a typical workday looked like. He didn't seem to have any real financial restrictions or obligations to anyone. He had the freedom to go where he wanted and do what he wanted.


On the one hand, this was enviable; on the other hand, it was suspicious. She didn't know if he had won the lottery, received a huge settlement in a legal matter, had taken early retirement, or was a trust fund guy. Maybe he'd gotten a windfall as an investor, maybe he was just jobless.


I coached her about how to "do discovery" and filter out men who weren't stepping up with appropriate and timely self-disclosure. From his perspective, he was probably being extremely cautious about disclosing his real financial status to women because he'd encountered some who were hungry for his lifestyle but didn't really know or care about him on a deeper level.


Make no assumptions. One guy might seem – on the surface – to be better off because he has a flush salary and a "finer-things-in-life" lifestyle, but he also has high expenses and tight cash flow because of alimony, child support, and non-liquid assets. That gives him less disposable income for dating. If he had a contentious divorce and the assets weren't divided fairly according to his definition, that could make him slow to trust and reluctant to remarry. Digging around for details about his financial station will only validate his distrust.


A slow, steady, and patient approach AND the willingness to demonstrate that you hold your own feet to the fire when it comes to career growth and financial ambition can help reassure him that you're interested in the man, not the money. At the same time, you can't invest forever in someone who gives you only breadcrumbs of information. (We can work out a balanced plan to handle this in coaching.)


If you can't resist the temptation to play “money detective” before or after your first dates, do it behind the scenes as much as possible; you may not be as subtle as you think if you’re asking explicit fact-finding questions. You could be inadvertently casting yourself in the role of "yet another money grubber" (if he's already met a few of these in the dating scene) without even realizing it. There is a time, a place, and an appropriate tone for a cards on the table money conversation between two people who are advancing toward a relationship.


Bottom Line: Get to know the real him -- the man who had a big brilliant idea or ran with a plan that made him the big bucks in the first place. Being interested in his passions and how his mind works is a better foundation to build a relationship on than a copy of his balance sheet anyway.