Starting a lasting love connection with someone includes being on the same page and having similar goals. Directing the flow of the relationship is difficult enough with all the quirks and bumps involving feelings and reactions, but there is one more factor that becomes an issue only when the couple considers it a big part of their bond: Money. Specifically, putting up a business together while you’re still dating.

I’ve encountered two separate situations where in my ‘investment’ in the relationship included something more than my attention and effort.

A. This guy used to come over every once in a while to watch movies with me in my apartment. He demanded nothing more than good conversation and the occasional smack, which was great because I didn’t want to feel preyed on in my own turf. Our meetings were always sweet and comfortable until one night, he caught me hard at work trying to figure out the squiggles in my income tax returns form and my bank passbook.

We joked around about how I’m not spending enough, and traded outrageous ideas on which market trends will skyrocket the coming year. He went quiet for a while then suddenly opened his notebook and started typing. My heart sank lower and lower as I realized that he was serious about starting a business with me.

B. I once hero worshiped a guy who embodies Superman’s energy and Batman’s cunning. When he finally asked me out, I sat there smiling and enthusiastic as he talked about his plans for the future (’our’ future, he said). He mentioned that he might just put up a business that will generate some profit during the 2 years that he’s still in the country, and without hesitation, I pledged my monetary support.

The business was sound. As expected, he handled it well and I, the silent partner, cheered him on. Trouble started when he increasingly became petulant, saying that I only called him to talk about our ‘biz. I soon got tired of explaining myself, but waited for our biz to break even before telling him that ‘maybe this isn’t working’. He didn’t argue.

What is the Focus?

A promising relationship and the potential of growing together are the similar elements in both situations. However, in situation A, I wanted to focus on the love connection more than the business; while the opposite was true in situation B.

Reflecting on the lessons I learned from these two almost-relationships, i can conclude that embarking on an enterprise together while still dating is a bad idea. The pressure of simultaneously maintaining a romance and keeping the business from plummeting may just be too much for a starting couple. I’m not saying that it isn’t doable, and more resilient couples may just make it, but mixing something as impersonal as cash during the time when both parties are still testing the waters could break the initial connection they felt for each other.