There are many ways you can get yourself introduced. One of the best ways is also one of the slyest, and I'll bet most people have never even thought of it: Put something you're buying into her cart - by 'accident.' Then simply point out your error when you want to talk.
o "Oh, wow, I'm just so overwhelmed with the choices for split-pea soup that I just helped you buy some, too. You don't have to thank me. I do this for all the shoppers."
o Or, "Whoops. I was about to put something healthy in your basket by mistake, but it looks like you might need it for real. Are you really going to eat that junk? Come with me, girl. We're going to the fresh food section."
Another approach is to run into her with your cart. (Hey, I never said you had to be sophisticated.) You just accidentally have a head-on collision with her cart. The trick of this maneuver is that you make it appear as if it were her fault.
o "Whoah! Ma'am, I'm going to have to ask to see your license and proof of insurance. I think I've got whiplash."
o Or, "Hey, are you the one that always runs into my car in the parking lot, too? I've finally caught you!"
You should definitely make it a point to shop around the wine section for a while. There is a lot of conversational opportunity here, and women love wine. Let the chumps shop for beer, you're here for the ladies.
o "Excuse me, do you know if you're supposed to have white whine with chicken?" And she'll say, yes. You ask: "What about with Cheerios?"
o Or, "Do you know what the difference is between a Syrah and a Merlot?" She'll try to explain, but it's always too subtle to understand. "Oh, I see. So you must be one of those people who stomps grapes in her basement, huh?"
Details: If you're still in your work attire (a tie and suit), relax it a little. Look like you're a snappy dresser, but feel free to get rid of the tie and put it in a pocket. If you're dressed in your best camouflage pants and Oakland Raiders jersey ... smack yourself up the back of the head and go get dressed. Your rule number one is to always go out dressed to meet the next gal you're going to bring home. You don't have to put on a tuxedo, but for gosh sakes, make sure whatever you're wearing is appropriate to the situation.
For a grocery store, you can show up in a pair of jeans and a t-shirt, but you better make it all look stylish and neat. Wear a decent pair of shoes (not your ratty Converse hi-tops) and a belt. Make sure your shirt isn't wrinkled, and your jeans don't look like they've been chewed up in the gears of your mountain bike.
Also, don't ever go to the grocery store with a wingman. You'll look gay.
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