A couple months ago (and to the shock and dismay of some of the folks with whom I conduct business on regular basis), I announced plans to jump back into the dating pool. Since “going public” or making my initial public offering (IPO), I’ve come to appreciate that dating is an investment strategy.

Does a high-risk, high-yield investment promise to net the savvy investor a range of compelling returns? Only time will tell. But let’s hope he has some meaty dividends. 🙂

I digress.  Dating is expensive.  There’s no doubt about it, especially in New York. Cue Bubba Higgins of the “Tri-State Area” on Mama’s Family circa 1987:

Match.com recently created an infographic about love and money, detailing what singles spend on their dating lives. Using U.S. Census figures and polling data, the company figured Singles in America spend a combined total of $82 million a year. The online dating service asked 5,327 singles (2,123 men and 3,204 women) to respond to a single question:  “How much money do you spend on your dating life per month?” They came back with $61.53 per single per month or what amounts to $738.36 per single in a year.

It’s not clear if those costs include advertising and self-promotion, but for yours truly, “keeping up appearances” is half the battle. I’m talking about everything from grooming to maintenance. Perhaps a new shirt is in order for a special occasion?

The new approach to my so-called “dating life” has forced me to take stock of my own position in the market. If I go out with this guy, will the value of some of my finer assets fluctuate? Take a dive? How will other would-be investors or spectators respond if they find out I slept with him on the third date?

And then there’s this question of how I’m playing the stock market. Monogamy has its appeal, but financial advisors always warn against putting all your eggs in one basket.  The best way to protect yourself is to diversify your portfolio (in this case, of men). I’ve applied that theory to the dating game (opting to see more than one guy at a time), and a part of me wonders if such a strategy should extend to romantic relationships altogether. I’m not whole-heartedly convinced.  But it occurs to me that by spending all our capital on just one person, we run the risk that we could lose everything if that relationship doesn’t work out.