Single in the South: 20 Questions by Chasity Boling


You’ve seen those eHarmony commercials where everyone says “I’ve met someone,” right? If not, you should google it. It’s annoying but let’s just say that’s true. You’ve met someone. Now that you’ve found a guy that you actually want to spend time with, what comes next? Sometimes, I feel like dating should have its own 12-step program. First, when you find a decent guy that’s worth your time, you meet and feel out the conversation to make sure he’s not a total weirdo. If he’s not a weirdo, ask yourself if the date warrants another. Second, if you decide to pursue, schedule more time to discover some common, (and probably uncommon) interests. Third … okay, maybe not 12 steps because that’s a lot of steps. Perhaps, a game of 20 questions would be better. A few to start with ...

•Do you like dogs? Personally, I always pray that the answer is yes.

•Do you have a criminal record? If the answer is yes, in the words of Ricky Ricardo “you’ve got some splainin’ to do.”

•Do you have a girlfriend? The answer sure as hell better be no if you’re trying to date someone else.

•Where do you work? Hopefully, they have a job. If not, again, they’ve got some explaining to do.

Of course, there are more important questions that you’re dying to ask but you don’t want to come off too eager. I think everyone has their own priority of answers when it comes to dating someone. For example, something that is very important to me is a person’s faith. My spiritual beliefs have always been a big part of who I am so it’s one of the few things that’s non-negotiable when it comes to finding someone to spend the rest of my life with. Other priorities may be how many kids they want or where they want to live. But when do we ask these questions?


Thoughts about personal life, family, career ambitions, kids, etc. … can be major deal breakers. You don’t want to sound crazy and presumptuous by talking about marriage and kids on the first few dates. Guys tend to spook easily and would probably run for the hills at the mention of long-term future plans after only having known each other for a few weeks.

And yes, there are some things that you find out along the way, which is the whole point of dating. However, there are also things that could totally blindside you, if you wait too long to disclose. This is something that I often wrestle with. I try to be carefree and live in the moment and not worry about these things. I try to let things fall where they may. But I’m also human, and a female, so of course my mind tends to wander to the future and what it might look like a few years from now. I don’t want to waste my time pursuing something that might be doomed from the start because we want totally different things down the road.


I feel like this hits females harder than males. It wasn’t that big of a deal in our twenties, but now in our thirties and forties, we have this damn biological clock that starts rudely ticking louder and louder. Guys don’t hear this clock because they can do whatever the hell they want at whatever age they want; but that’s another post altogether. Back to the question at hand, how do you bridge the gap between casual dating and an actual relationship, in order to ask those more personal/long-term questions?