Wednesday, March 28, 2012

"Double or Nothing": How to Date Two People in One Night

Since my time is valuable and I'm always up for a challenge, I decided to do something last night I hadn't done in a while--I went two dates in one night.  If you can swing it, this can be a good thing to try.  It's an efficient way of getting two first dates out of the way and if you don't click with either, you've only lost one night instead of two.

This wasn't the first time I've had a "Double or Nothing" date.  Over the summer, I met up for a morning hike and lunch with one man and then met another for afternoon drinks the same day.  It was easy enough to do on a weekend because there was plenty of time--I scheduled one date from 10am to 2pm and another at 3pm.

Last night proved to be a challenge because I had to work until 5:30pm.  I knew fitting two dates into the night was going to be difficult so I planned to meet one for drinks at 6pm and one for dinner at 8pm.  There was some very strategic planning involved, so if you're interested in doubling up, here are some tips.

Tips for "Double or Nothing": Dating Two People in One Night
  1. Pick two dates (one you like, one you're not so sure about)-- "Double or Nothing" works best if you are curious about meeting someone but not curious enough to waste an entire night on them.  Pick one date you like or think you'll like more (Date #2) and one you're just willing to give a shot (Date #1).  If your gut instincts are right, you'll be ready to leave Date #1 by your deadline.
  2. Stagger the dates-- You need enough time to get to know each other.  An hour and a half should suffice for the first--especially if you're not super interested in them.  Make sure to compensate for traveling time.   I planned my dates 2 hours apart, giving me over an hour and a half for Date #1 and enough time to travel to Date #2.
  3. Location--For Date #1, pick a location that is near, but not too close, to Date #2--something in the middle of your point of origin and your second destination is perfect.  A place that is en route to Date #2 is good because it cuts down on driving time.  Since you're not sure if you're that into him anyway, pick a place you at least know you'll like.  I picked a place I had been to on a previous date--it has a ton of beer on tap so it's an instant hit with men.  It was between my office (where I was coming from) and the location of Date #2.
  4. Excuse--Come up with an "out" so that you can leave on time.  Bring this up at the beginning of the date.  Don't lie, just keep it vague.  "I volunteer at a place nearby so I've got to leave at 7:30" worked for me.  It was the truth (I never said I was leaving to actually go volunteer; I just let him think I was), it gives you an end time and the subject is quickly changed to asking about the excuse.  "Oh cool, where do you volunteer?"
  5. Deadline--Pick and stick to your deadline.  If you go over, you'll be screwed for Date #2.  About 10 minutes before you have to leave, mention that you need to leave soon.  This gives you a chance to get the bill settled, go to the bathroom and leaves time for an awkward goodbye.  
Date #1 went as anticipated.  I had met him on Plenty of Fish, he seemed nice enough, offered to learn who Jason Aldean and Luke Bryan are and was pretty cute in pictures.  Our emails weren't anything to brag about so I figured he would be a good candidate for Date #1.   Right away I told him that I had a deadline to leave and he took the bait and started asking me about volunteering.

Conversation flowed but there wasn't any real spark.  He was also much cuter in pictures than in person.  I thought there might be some potential when he told me he drove a truck for work (you know how I love pickup trucks), but then I noticed that he was wearing one of those thick silicone bracelets (below) with the word "Groovy" written on it.  I have a feeling there was a story behind it but I wasn't up for giving him any positive reinforcement for wearing it and didn't ask.
Date #2 went better than Date #1, which was also anticipated.  I had met Date #2 at a bar last Friday night.  I was there for an intramural kickball event and he was there at a young professional event.  He was a tall, well-dressed, Billy Baldwin look alike and came up to make conversation while I was at a table with friends--bonus points for having the balls to come up to me in a group!  We engaged in some Yankees vs. Red Sox (go Sox!) banter and I gave him my number before he left.  

I met Date #2 for sushi in the town where I'm moving this summer.   I was looking forward to seeing him so when I got to the restaurant and he was no where to be found, I got a bit worried.  I quickly picked up my phone and called to ask him where he was.  Apparently he was peeing in the bathroom. Not exactly the way I imagined a man would be holding himself while thinking of me, but I'll take it.  He was soon out and after making sure he washed his hands, we had a great sushi dinner.  He even asked me out for a second date after I knocked a glass of water onto him.  

I'm exhausted this morning but happy that the "Double or Nothing" date worked!


  1. This is neat, I like that it makes the first date kind like a warm up or practice run for the second one! Glad you had fun- looking forward to hearing about your second date with dude number 2!

    1. It works well--my Date #2 over the summer went so terribly and I know it wasn't me because I was already warmed up and on top of my game! Turns out he was just awkward...

  2. Don't forget the most important rule! Don't have more than one drink with date #1

  3. And all you women complain that Men objectify YOU, you cannot possibly give both of these men the actual consideration they deserved. just had this done to me, three drinks in, plenty of flirting, she checked out my ass, I caught her and we had a laugh, then I paid the bill and we leave, later on I happened to find out that she went to the next date, was just tipsy enough, and she told him "fuck it, im in the mood lets go to your place" So very nice to fire up someones engine, so she can take someone else for a ride. Now I'm not in it for the sex, been chaste comin on 5 years now lookin for a woman worth my time, obviously I dodged a bullet with this one, but still it was fucking shitty, none of us are getting any younger, but there is plenty of time in a human life that you dont need vet two men in one go. Golden Rule, treat others the way you want to be treated.