The Fine Art of Buying Someone a Drink

by WiredBerries Editors — January 10, 2008

Flirting at the local bar can be a frightening or fun experience, but usually it's a bit of both. These days it can be either the man or woman who makes the first move. As a bit of a traditionalist myself, I believe that even if you're a woman making that bold first move of buying a handsome gent a drink, you shouldn't also ask for his phone number. If you hit it off, he'll bring it up before you part ways.

There are always risks. Just remember that it's a little like baseball--the homerun leaders are usually the strikeout leaders too. So just enjoy the process, and accept the possibility of "failure" as part of the fun. If the object of your attention isn't reciprocating, move on without letting it ruin your evening.

The "Geek Guru" David DeAngelo, author of Double Your Dating: What Every Man Should Know About How To Be Successful With Women, offers this helpful advice, "Most of the anxiety involved in approaching attractive women [or men] comes from the fear of the unknown and the fear of embarrassment or rejection. Once you actually approach a bunch of women and talk to them, you'll find that nothing bad is going to happen to you. This works wonders. Then, when you've gotten past your fear, you can lead the conversations toward getting numbers, etc."

However, you'll want to be careful that you don't appear to be a "predator" roaming around the bar looking for anything available--this is especially true if you have a group of friends nearby. You don't want the person you're trying to impress to feel like they're being surrounded by a wolf pack.

Instead, fly solo and take your time to size up the situation rather than rushing up to the "target." And don't stare or wait around forever. Once you get to the bar, find a spot that's close, but not too close, and relax for a few minutes. Check to see if the target does need a drink. If he or she already has a full glass, then "can I buy you a drink" can come across a bit lame. But if you get an encouraging look, head right on over.

Then, here's the really hard part: be yourself. Sounds simple but this is the biggest challenge for most of us. Almost everyone is looking for someone who is fun, smart, and easy-going, but no one likes someone who comes off as insincere, fake or showy. The easiest way to come off as sincere, is to be sincere.

There's no such thing as a surefire pickup line so unless you're really clever, stick with "hi," and then discreetly take a peek for a wedding ring. If there's no ring and no date around, introduce yourself right away. If you don't get a quick response, or at least a warm smile, you can be pretty sure that you're wasting your time.

If your target does reciprocate then it's time to offer to buy a drink. If the person agrees, you already have the makings of a natural conversation about drink choices, which can quickly lead into any number of topics.

If your target is part of a group, be sure to acknowledge his or her friends and include them in the conversation. Otherwise the group will probably close ranks, and your target will think you're rude too. On the other hand, if you play your cards right, the group of friends can facilitate the exchange. You won't have to do as much talking and your target will feel less threatened with a safety net of comraderie surrounding them. If the conversation goes well and everyone seems to be enjoying themselves, then politely ask your target if it would be all right if you got her phone number as the conversation starts to wind down. At that point, don't hang around unless you're sure your presence is completely welcome by everyone in the group. When in doubt, it's best to leave before things get awkward. Then call her within the next day or two two to schedule a time and place to get to know each other better.

The rest is up to you. Have fun!