To pick up girls at a resort, start on your first day and treat the place like the small world it is. The same few hundred guests share the pool, the beach bar, the buffet and the evening show all week, so a woman you say hello to on Monday will cross your path again on Tuesday. Use that. Keep the first conversation light, remember what she told you, and turn the second or third run-in into a plan for that night. Choose the right resort before you book, and head into town when the resort goes quiet.
Pick the resort before you pack
The resort decides most of your week before you arrive. A couples-only resort is full of honeymooners. A big family resort is wall to wall with kids and parents who are asleep by ten.
What you want is an adults-only resort with a social reputation, or a lively resort close to a town with real nightlife. Spring break weeks, holiday weekends and the start of summer bring groups of friends, birthday trips and bachelorette parties. Read recent reviews and look at the guest photos, not the marketing shots, and you will see who actually stays there.
Be seen on day one
Arrival day is when the social map gets drawn. Go to the pool, the lobby bar and the welcome party if there is one. Say hello to a lot of people, men and couples included. A friendly couple from the pool will introduce you to the three women in the room next to theirs faster than you could meet them alone.
The goal on day one is not to pick up anyone. It is to become a familiar, easy face, so that when you walk over on day two you are the friendly guy from the pool, not a stranger.
The pool, the beach bar and the evening show
The swim-up bar is the easiest opener at any resort. Everyone is waiting for a drink, half in the water, with nothing to do. "What's the best thing on this menu?" is all it takes.
Pool games and the beach give you a reason to join in. Volleyball, water polo and whatever the entertainment team runs at three o'clock are full of people who want to have fun. Play, joke around, and talk to the women on your team.
Sunset and the evening show bring everyone back together, dressed up and in a better mood. The bar right outside the show is where the night gets decided.
Turn the second sighting into a plan
The first time you talk, find out her name, who she is with and what she is doing tonight. The second time you see her, bring up something she said and suggest a plan. "We're heading into town to that bar on the water around ten. Come with us." Invite her friends too. Women say yes far more easily when the whole group is coming.
Do not wait until Friday. Every day you hold back is a day you do not get to spend with her.
How to hook up at a resort without making it awkward
A resort is a fishbowl. Everyone at breakfast saw who left the bar with whom. If you hook up, discretion is what keeps it easy for both of you.
Leave separately if she prefers. Keep it to yourself rather than telling the guys at the pool. She may be sharing a room with friends, so your room is usually the simpler option. The next morning, be warm and normal when you see her at breakfast. A man who acts cold the day after makes the rest of her week uncomfortable, and her friends will remember it.
Respect a no the first time, and leave the staff out of your plans. They are working, and many resorts do not allow employees to get involved with guests.
Get off the property
An all-inclusive wristband makes it tempting never to leave. That is a mistake. By eleven, many resorts go quiet, and the women who want a night out are heading into town.
Take a cab to the bar street, join the catamaran trip, spend an afternoon at a beach club. Each of these puts you in front of women from other resorts and gives you an easy plan to invite the women from yours.
Practice before you go
A week at a resort is a lot of opportunity, and most men waste it hesitating at the edge of the pool. The walk-over is a skill, and you can build it before the trip. Cold Approach holds its Bootcamp in Miami and New York, in the field from start to finish, with a coach reviewing every approach you make and telling you what to change. Group runs three days in a row at a ratio of three students to one coach. Private gives you a coach 1-on-1 for one, two or three days. Nobody needs prior experience, and getting men past approach anxiety is the specialty.
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.




















