4 Tips for Starting Conversations While Holiday Shopping

4 Tips for Starting Conversations While Holiday Shopping

December 18, 2009 11:57 AM by Maura Kelly


As promised, my favorite dating coach, John Keegan, has arrived over here at Maura Kelly HQ just in time for the holidays. His Santa-bag is packed with great, fun advice–for all you naughty girls and boys–about how to make the most of the abundant flirtatious opportunities that will surround you for the next week.

As John puts it: “Despite the fact that December means colder weather, it also means that most people are looking for chances to give, receive and create a little holiday magic. With a new year about to start, most of people (especially the single ones) are looking forward to new beginnings–which means they feel more open to welcoming new people into their lives.”

The other good thing about December, according to JK: “You know exactly where all the people are going to be–out shopping!”

* * *

BUT … before I go on, I feel like it’s been a while since I’ve told you anything too substantial about my life.
So … the really big thing right now is that my agent is sending out my novel to editors.
If an editor buys the manuscript, then a book with my name will be in stores eventually—though the whole process could take another year or two. If no one buys it, then … no book. It’s a pretty stressful experience, because I poured a lot of time (don’t ask how many years) and a lot of effort into writing the novel. To think that nothing may come of it is VERY scary. My agent is something of a big shot, if you ask me, so I can take some comfort in the fact that SHE loved my book enough to take me on as a client … but the editors are the ones who really matter. And we’ve gotten a few (very nice and very complimentary) rejections so far, which has me terrified.

There’s guy stuff, too, but nothing that can’t wait till next week.

A (very minor) preview: You should be hearing from Hot Band Guy (straight from the horse’s mouth) again very soon.
* * *
Now, on to the flirting advice.

What should you do if you’re out—at Target, say, or perhaps Banana Republic—and you see somebody that you’d like to get under the mistletoe?
John has three tips for initiating the conversation.

In the men’s department, position yourself fairly close to the dude you’ve been eyeing (perhaps he’s the one with the well-worn copy of Hamlet sticking out of his back pocket–hot!–or the one with Memento Mori tattooed on his forearm). Then pick up two items—two shirts, or scarves, or bow ties—in different colors, and ask your unsuspecting target what color he likes best. After he responds—“the green, definitely”—keep the banter going by telling him you’re trying to choose a gift for your brother, who is now a school teacher, or for your cousin, who plays experimental cello music. Then say: “Think he’ll like the green?”

Pick up a man’s shirt or sweater and approach your man. After explaining to the stranger in question that he’s about the same size as your brother or cousin, ask if you can hold the top up to him so you can get a sense for how it might fit. As you hold it to his shoulders, look him up and down before making eye contact—and telling him the shirt looks great.

If that feels way too bold … I understand. So ask instead if he would mind holding the hoodie (or whatever it is) up against himself, or even putting it on. Another option: Ask him to model a hat or scarf for you.

For those of us who are a little less daring—like me—John suggests inviting the man in your crosshairs to give his cultural opinion. In a book store, it would be completely natural to say something like “What’s a good new work of literary fiction that I can buy for my father?” Or, if you’re stirred up by a hunk who’s hovering in the poetry department, go over and say, “My favorite blogger thinks a modern poet named Jack Gilbert is very cool. But I don’t know much about him. Do you?”

Similarly, it’s completely natural to pop can-I-get-a-suggestion questions in the CD or DVD section of your local Worst Buy. For instance, you might say something like, “My friend Maura thinks I should get my indie-rock brother the new CD by The Horrors and this year’s Kings of Convenience album; what do you think is the best music to come out of 2009?”

Once you’ve initiated conversation, try to keep things going a minute or two. Being playful and light-hearted is best, but if can’t come up with witty one-liners, or coquettish questions, simply say something like, “Who are you shopping for? Let me know if I can help you choose a gift—you’ve been so helpful to me, after all.”


Before you even START talking to the guy, have a plan about when and how about how to end the conversation–that will make you feel like you’re in charge. (And you are!) After a few minutes, tell him you’ve got to rush home to make gingerbread men, but it was so nice talking to him that you’d like to do it again. There’s his chance to get your digits. But if he doesn’t do so after a beat–perhaps because he’s clueless, or nervous, or just not moving quickly enough–ask if he’s on Facebook, by any chance … or simply request his email address.

Then you’re out!


If any of you brave souls try this over the weekend, please let us know how the experiment works out.



ps: I have a fan page on Facebook, in case you are so inclined to sign up for it …


Rod-A-Claus: I will be expecting one S/F mask in my stocking, from you.

kissing santa

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