Treat the gaps in a work trip as your time to meet people. Sit at the hotel bar in the early evening instead of ordering room service, and eat dinner at a restaurant bar. Have breakfast in a cafe near the client's office, and walk a busy neighborhood after your last meeting. Being from out of town gives you an easy opener, and a woman traveling alone often welcomes the company. Be honest about how long you are staying and suggest meeting the same evening or the next.
Why a trip makes it easier
At home, men worry about who will see them. On a trip, nobody knows you. If a conversation goes nowhere, you will never see her again, and nobody you work with will hear about it.
You also have a built-in reason to talk. "I'm here for work and I've got one free evening. Where would you eat?" is a normal question from a visitor, and most people enjoy answering it. Women who are traveling are often in the same position as you. a dating coach notes that when a woman is traveling by herself with no friends in town, "now you're competing essentially against nothing."
The hotel bar and the lobby
Business hotels are full of people in exactly your situation: alone, finished for the day and a little bored. The hotel bar between six and nine is the easiest room you will find all week. Sit at the bar itself rather than at a table, so you can chat with the bartender and whoever sits down next to you.
Start with the situation. Ask what she is in town for, or what she ordered. If she gives short answers and goes back to her phone, leave her to it. If she turns toward you and asks questions back, you have a conversation. Keep it light and never hover.
Eat at the bar, not in your room
Room service is the most common way business travelers waste an evening. Find a good restaurant nearby and ask for a seat at the bar. Bar seating puts you next to strangers, often locals, and talking to the person beside you is normal there in a way it never is at a table for one.
Ask a woman nearby what she recommends from the menu, or what else is worth seeing in the city. Locals like showing off their town, and a good recommendation is an easy reason to ask whether she wants to come along.
Mornings, walks and the time between meetings
A trip has small gaps that most men spend on their phones. Breakfast in a cafe near the office instead of the hotel buffet. A walk through a lively neighborhood after your last meeting. The airport gate during a delay. Each one is a chance to talk to a woman who is not in a rush.
Daytime conversations in a strange city are relaxed, because you are a visitor asking a local about her neighborhood. Few openers come easier than that.
Conferences and client dinners
Work events on a trip are still work. A woman at a client company or in your industry may sit across a meeting table from you next quarter. Be friendly and professional there, and keep anything more for a setting outside the event, if at all.
An attendee from an unrelated company is a different case. Even then, the hotel bar after the sessions is a better place to find out whether she is interested than the expo floor with her colleagues around.
Be honest about the timing
At some point she will ask how long you are in town. Tell her the truth, and attach a reason to meet soon. "I'm here till Thursday, and I'm back every couple of months" is honest and leaves room for more. Only say you are coming back if it is true.
Then keep the plan short and specific. You do not have a week to spend texting back and forth. Suggest a drink tonight after your dinner, or tomorrow when your meetings end.
Practice before your next trip
The hardest part of all this is the first sentence to a stranger. A Cold Approach Bootcamp trains that in person, in the field, in Miami and New York, with live coaching on every approach and feedback after every set. If your work already takes you to either city, a Private Bootcamp of one, two or three days can fit around a trip, since Private dates are arranged after booking. Group is three consecutive days at three students per coach, and no experience is needed for either.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.




















