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Date on the Fly

If you are like me, there’s never enough time to get your social life in order.  After you’ve counted the drawer, put in your orders to restock and checked your dwindling stocks, you are bushed or get too involved with Top Chef Masters to concentrate on the most important things.  So, lining up a date can be a last-minute item at best.

But don’t let this discourage you.  The mobo approach these days is quite spontaneous.  In fact, excessive planning is frowned upon.  How can you enjoy an evening when you know what’s in store?  This does not give your romantic other any freedom.

So, making a date on the fly is a natural way to explore a budding relationship, or to inject new life into an existing one.


You either couldn’t summon up the courage to make a date ahead of time, or you couldn’t figure out who in the right mind would want to hang out with you for an entire dinner.   How can you find a date in a hurry, and yet not offend the date in the process?


Send a text to a couple of potential dates and see if you can link up with them.


The key in landing a date on the fly is keep it light and nimble.  You don’t want to come off as being desperate or wimpy, which you probably are.  But no need to broadcast it, right?

  1. In your phone’s contact, assemble a list of potential last-minute dates.  These are people who you know well enough to simply drop in on, or that have the potential of blossoming into more serious involvements.  If this is your romantic other, then the key is giving the date a bit more weight.
  2. It is recommended that to expedite this kind of dating on the fly in the future, you should tag your contacts with a code word that allows you to bring up the list with a simple search.
  3. Using your device, see what’s happening that evening.  There are usually good sources for this.  (See section 9.7 for more details.)  Look at movies, clubs, plays and restaurants.  Many apps and sites will list the ones that are close by.  For example, you may find the latest Cohen Brothers’ flick premiering close to an all-night deli.  Or, the latest Ridley Scott Roman epic opening near an Italian joint.  Or, if you are in my neck of the woods, an art flick down the street !  That’s a match made in heaven.  But be creative here.  This will help you.
  4. In much the same way you can match the movie and food, you can then match the person who’d best suit the combo.  Usually I start in reverse order (that is, with the person) then match the movie or event with a great spot to eat.
  5. Next, practice what you are going to say.  Yes, it is supposed to be spontaneous, but make sure you’ve got the lead-in right.  Start with a reason for the last-minute text.  Then, follow it with an open ended question.
  6. Next, if they are interested, suggest the combo.  Remember:  make it more than a single event so they see that you have something a bit more special in mind.  They’ll get the point.
  7. If they are busy or not interested, make sure you have a good way of easing out of the conversation.
      • It was definitely a last minute idea.  But let’s get together some time soon.  I realized I hadn’t seen you recently.
      • No problem.  Sorry that it was so spontaneous.  But I figure you’d be up for it.
      1. If your original idea does not fly, have a Plan B.  Another combo that they might like.  Remember:  just because it is last minute doesn’t mean that you wing it in your texting.

      Once your partner likes the idea, settle on a time and immediately give a call for reservations and tickets.  A lot of this can be done on your device.

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