How to Approach Women at a Rooftop Bar or Hotel Lounge

Dress cleanly, arrive like you belong, and open with something about the room. Rooftop bars and hotel lounges are quieter than clubs, so you can actually hear each other, and the women there are often dressed up and in a social mood. That makes them good places to practice. It also makes a try-hard approach stand out, so keep it relaxed, keep it short and spend your effort on the conversation, not on looking expensive.

That is the answer to how to pick up women at a hotel bar, written for the way a decent man actually does it: with a calm hello, not a performance.

a dating coach names rooftops as his favorite type of venue in New York when the weather is good. The open air feels freeing, and it keeps the music volume down, so a conversation is easier than in many clubs. A loud, packed club makes you shout. A rooftop or lounge lets you talk.

Venues with a bit of exclusivity have another effect. Women arrive in a more dressed-up mood, thinking of it as a bigger night out. a dating coach likes semi-exclusive rooms for this reason, since the crowd tends to be consistently good and the women feel a little special for being there.

A hotel lounge adds one more feature: many of the people there are travelers or locals out for a quiet drink, not a late night of dancing. Some are alone, and some are in small groups. That can make a hello easy, because they are away from their usual routine and often open to talking.

Do not try to look rich. A loud shirt and heavy cologne read as nervous. Wear clothes that fit, dress one level above casual, and keep accessories simple.

Arrive calmly. Say hello to the host or bartender like a normal person, order without apologizing, and then look around the room like you are enjoying it. A man who stands at the entrance scanning the crowd looks like he is waiting for permission. If you bring someone, one relaxed friend is plenty. A big group of men looks defensive.

At semi-exclusive places, you may get some push-back at the door. a dating coach says you need to be a little entitled and learn to deal with the doorman calmly. If it does not work, go somewhere else. Do not argue.

Read the room before you walk over:

• She is alone, or with one friend, and looks relaxed.
• She is not deep in a serious conversation, on a call, or visibly waiting for someone.
• She is looking around, enjoying the view or the drink.

A good first moment is when she is at the bar waiting for a drink, standing near the rail looking at the skyline, or sitting at the edge of a seating area. Avoid interrupting a table that is clearly in the middle of something.

Open with something about the shared surroundings. It is free, specific and easy to answer:

• "This view is ridiculous. Is this your first time up here?"
• "What are you drinking? It looks better than mine."
• "I can't tell whether the music is good or just loud."

Then add one sentence about you, so it does not become an interview.

Skip money talk, and do not try to impress her with the place or what you spent. A calm, easy manner will do more than any tab. One drink is plenty. Buying round after round starts to look like you are trying to purchase her interest.

If she is with friends, say hello to them too. a dating coach's rule applies here as it does on a dance floor: treat her friends as people, not obstacles. Spend a little time with the group, then give her more of your attention.

If the area is too loud to talk, suggest moving to a quieter corner, or let it go. A woman cannot get to know you if she cannot hear you.

If she smiles, asks you something back and stays where she is, keep going. After ten or fifteen minutes, suggest sitting down or moving to a quieter spot, and take her number before the night ends.

If she gives short answers, looks away or keeps mentioning her friends, thank her and leave. Do it kindly. You will probably see the same people again in a venue like this, so a gracious exit is useful.

The things that go wrong in nice venues are rarely about the venue. A man stalls at the entrance, hovers for an hour, or overplays his status. Each is a skill problem you can fix with practice and feedback. At a Cold Approach Bootcamp, night game happens in real bars and lounges in Miami or New York, mixed with daygame to suit you. Each training day is two four-hour blocks, with a coach beside you for live feedback on every approach.

Group runs three consecutive days at three students to a coach. Private is one, two or three days, fully one-on-one.