Dating Advice

Dating On The Downturn: Cashing In On Long lines

17 Comments 23 November 2008

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I had to wait for my sister and her husband to pick up a few presents to bring his relatives at the end of their flight to Mississippi. As I listened to a discussion on NPR about the economic downturn’s affect on retailers, I heard the phrase “super-long lines” and thought, what a great chance to meet somebody new!

Photo by Harry+

Photo by Harry+

I am encouraging you to approach your holiday shopping with the mindset of transforming interesting strangers into new friends for the following reasons:

1. Shared experience: You and that amazing brunette have been standing in the same check-out line for 20 minutes, listening to a baby scream three aisles over. This might be oversimplification, but they call it a check-out line because you check things out in it. You’ve been checking her out, now make a comment about your shared experience of the screaming. She’ll acknowledge you and probably give you a sympathetic smile or roll her eyes at the situation. This is your chance to move the conversation ahead.

2. Tangible Hints: That gorgeous blond standing in front of you in line with 17 identical stuffed animals in her arms? When she keeps dropping them, offer to hold a couple and use the opportunity to find out why she’s clearing the store of Ronnie Crocodile toys.

3. Captive Audience: The chance that she’ll give up her place in a crowded line just because you messed up your first attempt at conversation is extremely low. This means you might as well try again. Thank the shopping gods, think before you speak, and try not to be creepy. Odds are on your side.

Just making a comment isn’t enough, though. It’s important to move past the initial contact and encourage interaction. In a recent check-out line conversation with Connie (hate the name, adore the lady), I moved beyond the initial “shared experience” comment by talking about my shopping. I mentioned that I have a lot of sisters and sometimes find it difficult to purchase for them. Connie responded, as expected, by offering a bit of advice and comments on her own family.

  • Follow up on your initial comment with a question that cannot be answered by “yes” or “no.” This guarantees you a response of some sort.
  • Get contact information before your conversation has reached it’s logical end. In this case, it will be the interaction between your new friend and the cashier.
  • Be grateful and say “thank you” but don’t gloat too much while she’s still in sight. Your best bet is to just continue your conversation. Continuing the conversation after you’ve exchanged contact info is the best way to reduce any awkward feelings about the interchange and set any future contact up for success.

When I got home from meeting Connie, I rang up an old buddy who works in retail and had him find the item Connie had been looking for. I texted her with the information and offered to get stuck in line the following Thursday afternoon. You know what? She said yes and followed it with a bunch of annoying emoticons.

I knew I should have just called her.

Happy Holidays!



- who has written 34 posts on The Dating Papers.

S drinks a lot of tea and enjoys late-night walks on the beach. He lives with his beta, Balthasar.

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