There are some questions that you just don’t ask people, questions beyond the obvious ones like “How old are you?” or “How much money do you make?” When asked, some questions trigger responses that can linger in the air like a bad fart. I once innocently asked a cute guy I’d been flirting with at a bar why he was drinking bottled water.
Expecting to hear something generic – he was in training or had to get an early start in the morning – I was subjected to a twenty-minute diatribe describing not only his struggles with addiction, but also the origins of said addiction. And believe me, when you’re trying to pick someone up in a bar, nothing turns you off faster than the topic of childhood incest.
Dating makes you highly vulnerable to questions that you just can’t seem to answer, no matter how long you ramble. Like fumbling during a job interview, a simple question such as “Why did you move to Chicago?” can trigger an endless monologue on running away from a dysfunctional relationship revolving solely around alcohol, infidelity, and weed (trust me). Given that my lot in life seems to be eternal solitude, I, as the constant dater, have learned to dodge such open-ended questions. Question: Why did I move to Chicago? Answer: Work.
However, I was recently stumped by a rather crafty question while having drinks with someone I’d met online. Well trained in what is acceptable to say and what is completely off limits, I was stunned that I hadn’t considered this question in all of my preparation. In all my years of experience in dating, no one had ever asked me this: “Why are you single?”
I knew better than to take the easy route and blame my appearance. Even the most novice of daters know that a lack of self-esteem is not attractive. I also knew not to fault myself. Dating is all about the upsell, and nothing knocks down your sticker price like exposing your insanity and trust issues to a potential buyer. The question merited a response focused on blame. So not knowing who exactly to blame for my being single, I did what any over-educated American liberal would do. I blamed society:
• Every sane guy worth dating within my age bracket (25 – 35) is already in the throes of their first serious relationship.
• When those guys hit the market again after that first serious relationship ends, they will need a few years to resow their wild oats, which would then leave them pushing 40.
• 40 year olds have too much baggage. Their baggage mixed with my baggage will be way too heavy for any two people to carry.
• Catching younger guys before they get into their first serious relationship with someone their own age is not an option for me. Younger guys who like older guys do so because they have issues with their fathers or they like to spend someone else’s money. I’m too young to be anyone’s father and I’m poor, deeming me useless with the younger guys.
The tirade ended, and shortly afterwards, so did the date. I’d taken the long way around one of those questions best left unanswered. Now, moving forward, I know exactly what to say:
“Why are you single?”
“My boyfriend died.”
