You're out. You're having a blast and you just caught a glance from that pretty little something down the bar.
What do you do next? Be the gentleman that you are and send her a drink.
This isn’t as easy as it sounds, though. You’re aiming for suave, not sleazy. But if you play your cards right, you’ll be able to make a big impression with your gentlemanly style and confidence.
Use the bartender as your wingman
To pull this off correctly, it’s essential to get the bartender on your side. Make sure to treat him with respect and not like a lackey. After all, his delivery will go a long way to determining how the woman is going to react. If his body language says you’re a jerk, it doesn’t matter what words he uses when he brings the drink over to her. When sending women drinks, the bartender is your wingman and in order to make him a helpful and willing one, you should be nice and tip big.
Ask what she’s drinking
You can’t just order any old drink and send it over to her. You should ask the bartender what she’s drinking and send another of the same to her when it looks like her drink is getting a little low (but before she orders a fresh one). If you end up choosing something she doesn’t like, you’ll have wasted a drink and won't get the reaction you desire.
Play it safe and send her something you know will please her taste buds. Another way of doing this is to ask the bartender to charge you for whatever drink she orders next. When he hands it to her he can gesture in your direction, indicating that it’s on you.
The casual nod
As the bartender takes the drink over, keep your eyes on the woman. When he points you out to her, put on a genuine smile and give a casual nod. You could also slightly raise your glass toward her. Don’t jump up and down or wave at her like a lunatic. You don’t have to act overly eager. Just keep it cool and sincere.
Observe her reaction
The next step is to watch her reaction to see whether or not you should make your way over to introduce yourself. If she returns your smile and waves, you’ve got a green light. If she turns to her friends and giggles, give it some time to figure out whether she’s laughing at you or expressing her delight to the girls. Anything along the lines of eye-rolling, nose-upturning or refusing the drink is obviously a bad sign. In that case, shrug it off.
Introduce yourself
Give her a chance to enjoy her drink. Then, if her reaction is favorable, approach her and start up a conversation. You shouldn’t act cocky or assume anything just because she accepted your drink. You have created yourself an in to start things off with her, but don’t take it for granted. You still have to use your wit and charm to make a good impression. A proper follow-up is key when it comes to sending women drinks.
the ice is broken
Sending a woman a drink is a classic move that many women will appreciate. It’s an old-school gentlemanly move (you know Clooneywould approve) that doesn’t get used too much these days, and therefore has some novelty appeal. If you feel like taking a more direct approach, you could just go up and talk to her, but sending over a cocktail first will make her feel special and show her that you’re a generous guy. Sending a drink over will definitely provide you with an easy icebreaker.
From there, it’s up to you to form a connection and get her interested in you.