3 Easy Ways to Make a Conversation More Awesome

... even if it's not going that well.


At some point in the recent past, I may or may not have gone on a pretty fun date with an Internet cowboy. (However, having learned my lesson, I'm going to stay tight-lipped on the topic.)

But let's just say, for the sake of argument, that my date did NOT go terribly well--that we were struggling to make conversation, feeling awkward, wishing that we could be home clipping our toenails. If it had gone that badly, would there have been anything I might have done to make it more awesome?

Yep. In her new book Meeting Your Half-Orange: An Utterly Upbeat Guide to Using Dating Optimism to Find Your Perfect Match, my old pal Amy Spencer has some good ideas about how to add a little piquancy* to a conversation that's gone flat.

1) Commit to complimenting your date on three things.

Now, I'm not saying (and neither is Amy) that you should be a driveling sycophant.* Don't lie. Don't gush. Don't go over the top. But do make an effort to voice any positive impressions your date has made on you. For instance, you might just want to say: "That's a great sweater--I like that it zips up." Maybe what you like is the slightly rusty sound of his voice. Perhaps you could praise him on the great work he's done, building up his beer belly. ... Or maybe not.

But seriously: Fill him in on his good qualities. Why? There are few people in this world who aren't happy to receive compliments. What's more, your warmth could encourage him to let his guard down--and allow the dialogue to flow more freely. Plus, you immediately make yourself more likeable.

2) Ask questions.

If there's anything that people might like more than being complimented, it's being encouraged to talk about themselves. So if you feel the chit-chat flagging, start quizzing him. Can't think of anything to say? Here are some questions you could try:

-What's the scariest thing that happened to you this week? (Or this year. Or in your lifetime.) What's the weirdest?

-What's the best trip you've ever taken? Why was it so great?

-If you had to leave town tomorrow forever, what would you miss most about this place?

But what's just as good--perhaps even better--is asking questions that the conversation (or the person) naturally suggest. If he's from a foreign country--or simply another part of the country--ask him what life is like out there. Ask him to tell you the coolest thing about his neighborhood--or about his dog. And so on.

3) Use the evening as practice for getting better at being yourself.

If you're like me, you're so interested in being easy-going that you never want to be difficult ... Which means you sometimes agree to go to a coffee shop when what you really want to do is be at a dive, playing good songs on the juke box. Or vice versa. Or you agree to Mexican when your stomach is feeling sensitive and you'd rather just get comfort food. Or you agree to walk 600 blocks to find some stupid hole-in-the-wall that he's excited about ... only to get there and realize it's closed. NOT that that has ever happened to me.

But as Amy points out, being able to easily and consistently voice your needs, thoughts and desires is crucial to maintaining a healthy relationship. (Otherwise, you make yourself miserble, bottling things up all the time--until you can't hold it in any more, and you explode, and there's lots of drama.)

So if you're on a date that you know is going badly, use it as an opportunity to be upfront about what you want in the world. (You should always be doing this, really, but it can be hard--which is why you should practice on an occasion when the stakes are low.)

What do you think, lovelies? Is this sound advice?



Dictionary.Maura :

piquancy: a little oooh-la-la, spice

sycophant: ass-kisser, boot-licker, suck-up


dear commenters:

-first off, I love that all you nice people on my Fbook fan page are such good readers. and i love that there were so many good responses to my question. looks like i might have to do some kind of post on the topic of best love quotes ...

-Rob! i am so not surprised to find out you are a cab-necker. cab-necker. i think this needs to be a new term. you cab-necker!

-and Kell: i'm of the opinion that there's no such thing as too old, or too young ... especially when it comes to firemen. if you connect with the guy sexually, intellectually and emotionally, i don't care what age he is. do you think? just make sure he's not trying to take advantage of your youth and innocence! but it sounds like you were the one in the, er, driver's seat, so to speak.