When people ask this sort of question what are they expecting to hear someone say? The complexities to why most people are single are much more detailed than what a brief sort of whimsical response can really sum up.  And the only thing sillier than someone asking that question as some sort of easy segue into common conversation, is someone who actually wants the detailed information.  You know the type.  You respond to that question with a smile and a modest sort of answer to just slide through the awkward moment and some clown hits you with a follow-up question which basically asks you the same thing in a different way.  What they hell do you expect from me?  A full detail of my dating failures since I was 18? I have hear this question from women plenty of times.  But this lame sort of questioning is not unique to the fairer sex.  Both men and women ask the question.  Just from different angles, with the hope of getting slightly different responses.

Men are the worst at asking this question.  They usually ask it as some weird sort of icebreaker because they think that it is flattering.  They are asking it under the tone of asserting that a Woman as fine as you can’t truly be single……Someone had to have scooped you up. (btw…as much as I want to say that is super corny, I have seen more than a few guys get that off and send a woman into some sort of blushing hysteria) Now a lot of guys like to ask this question in a flattering way to avoid just asking flat-out, “Are you seeing someone?” Asking a woman are you seeing someone is a yes or no question.  It could potentially just flat-out dead the conversation right then and there.  But to flatter a woman and ask her How can a woman as beautiful as you be single, allows a woman to give a more expansive sort of answer which will carry the conversation further and hopefully ensure that he will not get a door slamming direct sort of conversation ending response.  Because a lot of times guys don’t really care if you are single or not.  They want to see how tied to the situation the lady is.  Too examine whether or not there is wiggle room for him to slide into a cozy little position.  However, the mistake that guys make is when they get the woman to not slam the door in their face and seem open to continue a conversation, they hit her with the follow-up question.  A woman gives a casually polite sort of response like…Well I guess I haven’t met Mr. Right yet. Instead of taking that as a green light with her saying…Ok, you are somewhat attractive and not a complete turn-off to me so continue to speak, guys hit ladies with the follow-up commentary and the whole thing just spirals out of control.  I’m just saying, a woman like you doesn’t walk the streets without a man. Something just can’t be right! Bad, bad , bad move.  Now, with this statement, a man has done one of two things.  He has either opened the flood gate for this lady to poor her heart out about her past situations which neither of you should be discussing at this point or you have put her on the defensive as she feels a tad bit insulted because it sounds like you are insinuating that something must be flawed about her.  C’mon son…  The irony of this is that when guys hit women with that follow-up question it’s because their smooth playa, mack-daddy game sort of stops right there.  Most men aren’t nearly as smooth with the rap game as they think they are.

Now with women, the tone of this sort of question seems to be the same.  The initial line of questioning starts the same way.  Lady asks the question…guy gives modest response and tries to laugh it off as a complimentary statement.  But that is definitely where the comparison stops.  And I mean a dead stop!  It has been my experience that when women ask you that question, they really want to know! They aren’t complimenting you.  They aren’t making conversation.  They are looking you up and down with the intent on immediately uncovering the character flaw that made the last woman get rid of your ass.  And when you try to move away from the questioning they will indeed horse collar your ass back into the discussion.  I might respond with, “I guess I am single because I haven’t been that lucky yet (smile).  So tell me about you.  What do you do?” And she will get me right back on topic with,   “Well I’m a Contracting Agent for the government but that isn’t nearly as important right now as you telling me when was the last time you were in a relationship.” ………. Awkward………  Now I feel like I am on an interview.  And in DC women want to know it all.  They want to figure out if you are unemployed, dating multiple women, secretly dating a man, do you have any kids, baby momma drama, police record, emotional instability, mommy issues, daddy issues, car trouble, a place of your own, a weak bladder, boring hobbies, legal citizenship…..etc…  I mean they really want to know it all! And I think that women are definitely entitled to know about someone…….but damn! We literally laid eyes on each other like 10 minutes ago.  You can’t ease into this stuff?  In a woman’s attempt to try to figure out why a guy is single, a lot of times she clearly shows why she is single.  The psycho, pushy, interrogation technique typically does not go over too well with guys.

It’s not like the question is entirely a bad question to ask.  But it is easy to see why people are put off by the question.  It’s like asking someone, why aren’t you working or why don’t you have your own place.  Maybe the person you are asking the question to wants to be with someone and they just can’t make it happen right now.  And maybe they are disappointed by it and don’t really feel like having to explain that whole thing to a total stranger.  We can all relate to that.  And most troubling is the immediate mindset that something must be wrong with a person who is single……….meanwhile…you are single.  My bad…I forgot.  You are the exception.