Over-Fifty Flirting – It’s Like Riding a Bike

Being a Suddenly Solo will open up opportunities to make new connections… some romantic, others not so much.  But no matter where it leads, without taking a first step, you just wind up exactly where you are standing. Flirting is an accepted introductory mechanism in our society, but there is definitely a subtle balance to the interaction that you must be mindful of, lest you come across as creepy or downright scary.  Nonetheless, much of the mechanics of flirting are the same as they were when we were younger.  However, the odds are now stacked in our favor since the number of available women outpaces the number of single men as we have aged.  This should give you the confidence (see below) that is so important to effectively making an initial connection.

Here are some tips that might help remind you of how to get back in the game:

  • Make eye contact.  Here, it is actually okay to get caught looking!  Don’t leer or stare at her; throw occasional glances until your eyes meet.
  • Smile.  When you make a visual connection, hold the gaze for a moment, smile and then look away.  Repeat the cycle a few seconds later.  Keep your smile warm and not “grin-like.”  Women respond to slow smiles… and nice teeth! If you are met with a similar reaction, go over to her – smiling.
  • Initiate conversation.  If you are focused on a stranger you will likely not see again unless you seize the moment right then, go over and say something like, “Definitely crowded here tonight, right?” or a similar non-overt opening.  If the lady is someone you have seen regularly (i.e., at work, a class or routine scheduled gathering), perhaps wait until the next time you are together to start the conversation – it’s a build-up.  No matter when you speak to the lady, the first line is just an invitation to engage in conversation.  It doesn’t have to be a pick-up line.  Like the line above, it is just to start things off.  You may be rebuffed, but no harm, no foul.  If she is cool and not interested, just excuse yourself.   However, if you do start to chat, keep it light. No politics, religion, etc.
  • Body Language.  Be accessible. No arm folding or fidgeting.  Face the person you are speaking with.  Remember, you want her to feel comfortable around you and if you project an easygoing aura, she will feel at ease as well.
  • Be complimentary. No flirting is complete without a healthy dose of compliments.  For example, “I am really enjoying speaking with you.  You are so knowledgeable on so many topics.”  Maintain eye contact and speak in the lower, more bass part of your vocal register.  NOTE: Be careful about complimenting her looks beyond her eyes, hair or hands.  This is way too early to compliment her on her figure!
  • BE CONFIDENT.  The days of being coy are beyond us.  While you don’t want to appear overbearing or obnoxious, if things are going well, then you can probably go all-in with something like, “I hope I’m not being too forward, but I have to say that you are really an amazing person.”  No guts, no glory.
  • Spread the wealth.  Flirtation should be an ongoing exercise over a period of installments and not necessarily an all-out, one-on-one effort.  In fact, these initial conversations that go on for more than 5 or 10 minutes may easily bog down into an uncomfortable silence.  Keep your interactions brief and don’t over-stay.  End with something like, “It has been wonderful chatting with you.  I hope we can see each other again,” and see how that goes.  We mature single men are in demand these days, so don’t think you have to ask for a date on this first foray into her world (although if your relationship radar is flashing that she’d like to go out, then by all means, go for it!).
  • Take it in stride.  Flirting is supposed to be fun.  Take the nice interactions along with the strike-outs.  Stay positive, take a breather after strike three and chat with the bartender or the party host and re-group for another outreach.  You will get better and better at it as you put yourself out there… we promise!


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