You don't have to be good-looking or funny or smart or obviously wealthy to pick up a woman in a bar. Living proof right here.
Get there about 7. Early enough to find two empty stools at the bar. Sit down in one and place your blazer over the back of the other. It's not necessarily required that you do this while on a business trip, but it's what seems to work for me.
Then order a drink and ask for two menus. Scan the menu, check your watch, fiddle with your shirt buttons (top button unfastened... no, better keep in buttoned), check your phone to see if you missed any calls, glance toward the door every time someone enters.
Things will start to get busy. The bar will start to fill up.
Eventually, someone will ask if the seat next to you is taken. Maybe its a man. Maybe its a woman. Doesn't matter. Just apologize and tell them you're waiting for someone.
Order another drink. Maybe 30-45 minutes have passed by now. Check your watch a little more frequently. Another beer. Then order an appetizer. Look at your phone again. Pretend to leave someone a pathetic voicemail ("Hey, just checking to make sure I heard you right - 7PM at The Charterhouse. Please give me a call when you get this.... oh, and if you're on your way, let me know and I can order for you so you don't have to wait. I was running late anyways, just got here. Ok?"). Another drink.
She'll have started paying attention by now. She will self-select.
She'll probably be with a group of friends. All of them will be sneaking glances and whispering back and forth, but she'll be the one with the look of empathy and concern. Do NOT make eye contact. You're just focusing on who is NOT there rather than who is.
She will ask if the seat next to you is open. Pause before answering. Look towards the door. Check your phone again. Exhale barely audibly, remove your blazer from the stool and say "yeah, I guess it is".
Immediately summon the bartender and order another beer. This is when you stop glancing towards the door and looking at your watch. You will feel her looking at you.
She'll eventually break the ice, saying something like "Maybe she's just running late" or "Don't feel bad. We've all been stood up before" or "She must be an idiot". Flash a quick smile, a little laugh at most.
Say something self-deprecating.
By now, the following thought will have already crossed her mind;
"This will be such a cute story to tell people about how we met - he was stood up by his date, we started talking, hit it off".
Much cuter than "we met in a bar on a Thursday night".
After a few minutes, ask her to save your seat while you go to the men's room. Don't refer it it by anything other than that; the men's room. Not "the little boys room". Not "the head". Not "the bathroom".
The men's room.
Take a couple steps towards the men's room, pause for a second, then turn around to ask her, "hey, if you see a redhead, about 5'8" walk in, can you please tell her I'll be right back?".
Pathetic.
You'll come back. She will have saved your seat. Don't sit down though. Reach for your jacket, thank her, and tell her that you're gonna take off. She'll grab your arm and ask you to stay, maybe just have one more drink. Her treat.
Slowly open up. Share a joke. Let her cheer you up. She'll say something bad about the girl who stood you up. You say,"No, no, no. It's no big deal. I'm over it".
That's it. Yours. Without fail.
