How to pick up a hotel bartender (and leave with your dignity)

You’re traveling for business or pleasure and booked into a swanky hotel in a world-class city or resort with all the amenities, including the bartender you noticed your first night at the hotel bar.

It was lust at first sight.

Hotel bars are a cut above your usual haunts, from your local gayborhood spot to the dive bars you’re partial to. Business deals are being hatched over drinks, wedding parties mingling, and theater types might get a cocktail before or after the show. The hotel bar is a crossroads, and your bartender stands in the middle of a bustling intersection.

Pack your bags, we’re going on an adventure

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On your first night at the hotel, you saw him from a respectable distance, over cocktails in the lounge with fellow travelers who’d taken in the sights that day. Their stories became a muffled soundtrack along with the standards from the polished grand piano across the room. There he was, in the soft glow flashing his bright, cocky smile.

You must have him.

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But picking up a hotel bartender can be a tricky dance, and missteps are common.

Here’s a guide to help you make a successful first impression with your hotel bartender while keeping your dignity intact.

1. Dress for the occasion

After your first night’s reconnaissance, you’ve got a leg up on the vibe in the room. Read it carefully, and dress accordingly.

Don’t wear your regular outfit to go out slutting; no one wants to see your midriff in a classy place like this.

If everyone in the room is wearing a jacket, wear a blazer/polo combo; you don’t want to be the odd man out when you finally introduce yourself. A well-fitted polo shirt will do if it’s summer or a resort. A V-neck cashmere sweater over a crewneck t-shirt says casual but sophisticated if it’s chilly.

2. Respect the professional vibe

Find a seat at the bar where you’ve seen him serve and wait for him to find you.

Do not try to get his attention. Do not flag him down. Do not wave. Do not point to a glass. He does speak English.

First and foremost, he’s there to serve you, so let him do his job before you start doing yours.

3. Be patient and observant

Your bartender is likely balancing guests and maybe multiple languages, along with hotel protocols, while you wait to be served. Don’t expect or demand undivided attention. He’s a professional and knows what he’s doing. Scan the drink menu and stay casual.

4. Order something interesting, but not too interesting

Do not order beer unless it’s Oktoberfest and you’re at a Four Seasons in Germany.

Make a selection from the bar menu that’s simple but sophisticated, and maybe has a local angle that you can inquire about later. Cut him a break and avoid anything blended. Besides, the noise!

5. Keep the conversation real and relevant

Forget your best pickup lines, as successful as they may be.

Break the ice with something he can respond to genuinely. Ask about that local angle on your drink. If he’s good at his job, he’ll have the details behind your cocktail down and be enthusiastic to share them. Drawing out his expertise is a sign of genuine respect. Authenticity usually wins.

6. Keep it light

Your bartender has been around the block — that’s just the nature of the job. Stay casual and affect interest without outright obsession, which he’s doubtless been subject to before, because look at him. Let him be charming first — and meet his charm with your own.

7. Read him carefully  

Hotel bartenders must stay professional, no matter their genuine interest in their guests or lack thereof. Remember this as you assess the possibility of moving your engaging exchange beyond the bar.

Are you asking all the questions, or is it a two-sided conversation? Is that laugh at your latest observation pro forma or genuine?

Watch him with other customers between chats; is there something special about how he treats you? If he’s smiling and truly engaged, great. If you sense anything less, start to reappraise your obsession.

8. Stay local

Move the conversation beyond the bar subtly by asking about something local. Not like where he lives or where he’s from (not so subtle), but a spot or something to do that he finds interesting and isn’t a run-of-the-mill tourist destination. That opens the door to his own interests and maybe some of those you share with him.

9. Know when to fold

If you’ve gotten this far and are on your second or third drink, things are moving in the right direction. If things aren’t clicking, and your interests and attraction aren’t shared, tip him well and wish him a good night. You’ve got a week left in town, and you’re only warming up.

You’ve maintained your dignity.

Besides, you can always stop by another night to see if you really did misread the signals. If you didn’t, don’t be a creep.

10. Suggest a change of scenery

If the signals are correct, suggest continuing your conversation elsewhere.

He won’t do that; hotels frown on fraternizing with guests. Even if he wanted to, he would unlikely make the first move. You could be a narc, as charming as you’ve been.

Suggest getting a drink at that after-hours spot he shared with you, or discreetly slip him your room number if the vibe is urgent. He’s off at midnight, he might tell you. Can you wait until then? Of course, you’ll tell him as you sign a fat tip. You’ve waited this long.

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