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A few years ago, a friend of mine started dating a guy who was funny, personable and driven (at least he seemed to be). He had big ideas and seemed like he was going to be determined to see them to fruition. When they first hooked up, he had no steady job. Still, my friend and I, along with others, appreciated his hustle, as he was an aspiring entrepreneur.

Instead of getting a job, he got random gigs here and there to create a stream of income. And as a girlfriend, my friend’s support of this man was unwavering. When he didn’t have extra money to take her out, she would often foot the bill, and when he needed a second opinion for a business decision, she provided an intelligent and unbiased one.

Things were going well but I could tell that my friend started was starting to get weary. Eventually, she realized her constant encouragement was going in vain as he continued to talk a good game but never did anything to propel his business aspirations.

Two years into the relationship, she called it quits with him. Although his lack of ambition wasn’t the sole reason for the demise of it, it was the biggest issue.

This friend of mine is a rarity, as some of my other girlfriends would have never even wanted to give a guy like this a chance. Many of them have stated that they want to date a man who “does well for himself,” and some mainly want a man who makes more money than they do. I can’t fault them for that, though. I’m sure most women would look the other way if a man interested in them, who claimed he was “starting a business,” didn’t have a steady job. And after two years, it just wasn’t acceptable.

I had to give my friend props for at least giving the man a chance to live out his dream, but at what price? Did she ultimately waste her time? She doesn’t seem to think so.

Once they broke up, I asked my friend if she would ever date someone again who is in the process of building their business or pursuing their dream. I expected her to say “hell no,” but to my amazement, she said she would be willing to give another man, in a similar situation, a chance. However, I’m sure her vetting process will be a lot different.

As a person who has always had an entrepreneurial spirit and has attempted to start a few businesses, I can appreciate one’s drive. You can’t knock a person for dreaming big, but that doesn’t necessarily mean you have to ride through the ups and downs of making their dreams come true with them. So, if you find yourself wanting to date someone who is between jobs or is chasing their passion, I suggest laying everything out on the table in the beginning. Inquire about their goals and the timeline for each one. Do they have a plan B?

Even think about how long you can ride this wave and how supportive you can be. Be honest about what it is you can deal with and what’s just not for you. If you aren’t down with it, it’s ok to not mislead anyone by pretending that you are.

Knowing what you’re getting yourself into and choosing to stay, or not stay, based on the information gathered is smart. It can save time (and hurt feelings) in the long run.


Image via Bigstock 

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