The 25 Date Week

Unless you are one of those fortunate individuals who thrive on the up and down roller coaster that is dating (and in which case, it’s unlikely that you are reading something by me), there’s a strong chance that you have at some point in your life been stuck at a dating crossroads trying to decide what to do next. 

Maybe you just got out of a relationship, or have moved to a new city…maybe you have been dating for awhile but can’t seem to get past 2 or 3 dates.  Whatever your particular scenario, there is hope – and better yet, actions you can take! 

Dating is a skill that can be learned.  True, some people seem to have a better knack for it – but overall, the behaviors that contribute to successful dating can be refined just like when learning an instrument.  And here’s the inevitable platitude and cliché when using an instrument metaphor…yes, you have to PRACTICE.

Regardless of your particular objective – whether you want to enjoy the scene and play the field or whether you are actively seeking a lifetime partner – one of my first recommendations is to try a 25-date week.

In this day and age, we are masters at scheduling.  At work, we go from meeting to meeting with barely a breath and a nabbed extra bagel in the conference room along the way.  At home, we ferry children back and forth to lessons, school, and other activities.

Give yourself a week – just a week – to turn that scheduling skill into a chance to improve your dating skills.  Here’s how…

  • Choose a week about two weeks in advance, clear all other non-work activities, get a babysitter on call, and budget an hour per date.  Divide each evening into three timeslots – after work happy hour, dinner, and after dinner drinks.  Add a few weekend brunches and/or afternoon coffees and you have 25 hours that you can fill with first dates.
  • Log in to Match.com (or any other online singles matchmaking service – note that because we are looking for quantity at this point, eHarmony may not be the best option because of its exclusive matching function – it has its place and value but not necessarily in this exercise). 
  • Flex your confidence muscles and initiate, initiate, initiate!  Wink or send emails to anyone interesting – my first time on Match.com, I had 50 pages of men interested in meeting someone ‘like me.’  50 pages!  It was a catalogue of men!
  • Use this time to experiment – wink or send emails to some people who may not typically be on your radar screen.
  • Accelerate suggesting meeting in person.  Be VERY clear as to your timeframe when scheduling – ‘let’s meet for one drink,’ ‘I can’t stay out late but how about a quick dinner at 7,’ etc.
  • WRITE IT ALL DOWN – in a calendar, excel spreadsheet, poster, whatever works for you.  Not only will it help you keep it straight, it will be a fantastic memoir of your whirlwind week.
  •  And then…jump in.  Some will be great, some will be failures….but you’ll have broken the barrier that kept you flummoxed.  Make sure to stay on schedule, practice exiting gracefully, practice suggesting another date if you truly want one, practice, practice, practice.  Oh, and control your alcohol intake – unless you hire a driver for the week, you’ll want to drive so you can control the schedule.

And then schedule a few days to debrief and rest.

Special Note:  My apologies to any men out there who recognize that they may have been part of my OWN 25-week date when I moved to Charlotte.  Please know that I enjoyed each and every one of you…

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