Friend's Friday - Conversation Starters

Cover Girl - Caitlin last Thursday in Palm Beach 

Whenever Rhonda and I go out we make a special effort to talk to people.  We talk to the folks next to us at the bar, at the table next to us, the wait-staff, the taxi driver, the doorman…anyone we meet.  And we’ve had some VERY interesting conversations and met some very interesting people…it’s such fun!

Twelve years ago I had never spoken to any other human being while I was dressed…and I’ve been dressing since I was five years old!  I just couldn’t stand the isolation anymore and I decided that my life in the closet had to end.  So I bucked up the courage to speak to people and that act profoundly changed my life.  I remember going into a restaurant with a group of trans women at the first Keystone Conference in Harrisburg.  

A woman who was with her husband at the bar gave me a glance and a smile as I passed by.  When we returned from dinner she was still there.  She smiled.  I smiled.  I said, “I’ll bet you have a question…” Her face lit up and she said, “oh, I do!  I do!”  We spent the next hour talking about what it was like to be trans.  I guess that’s where it all started.  “I’ll bet you have a question…” is just perfect for women…especially married women in the company of their husbands.  It’s non-threatening and if they don’t want to talk they can simply say, “no, I don’t have a question,” I’ve probably used this conversation starter a hundred times over the years and I have yet to find a woman to say, “no.”

There are lots of other conversation starters, of course.  I try to form questions that are a) open-ended (so I don’t get a “yes” or “no” answer), b) that are unusual or even just jarring enough to make the person turn off their “autopilot.”  Let’s list a few below:

• If you were in charge of the playlist, what song would you play next?
• Why did you come here tonight?
• What’s your favorite part about living here?  What’s the least favorite?
• Do you think [this city] is a place most people move to or move from?  Why?
• What do you miss most about leaving your last town…and what were you happy to leave behind?
• Since you live here, what [restaurant, event, museum, points of interest] should I try not to miss.
• If you had to switch outfits with one person here, who would it be?
• If you could live anywhere in the world, where would it be?  Why?
• You remind me of a celebrity, but I’m having trouble remembering their name…Who are you normally compared to?
• I’ve got a big decision ahead of me and I could use your advice.  Should I have [Appetizer #1] or [Appetizer #2]?  Smile.

There is probably nothing better than a friendly smile to start any conversation.  Showing others that you are approachable and open signals that you are interested in engaging and that you won’t reject them.  Try a few of my questions the next time you’re out.  You may be pleasantly surprised by the positive response you get.  Success builds success.  

Hugs to all,

Caitlin