Follow these rules, and your chances of having a successful man date will go up dramatically.
1. Be a man.
Men have good hygiene, make eye contact, and respect the people they spend time with. Men are not possessive or insecure; boys are.
Men like to hang out and get to know each other, so the last thing you want is to be sitting with your bud and have the conversation dry up, leaving you bored with each other for the rest of the time.
Think about your friend and what you would like to know about him, and in return what you would like him to know about you. Try to think of any questions that he might ask you, so that you can prepare the answer. You might think that it is easy to talk, that you won't run out of questions to ask, or that you will automatically have the answers. But until you're in the situation, you have no idea what it will be like. Practice if you can.
One great way to avoid this kind of situation is to plan an activity to keep you both occupied. One of the most popular places for man dates is the football field. If your town has a professional football team, you can go to the game on Sunday afternoon. No matter where you sit, the atmosphere will be perfect. You can scream and yell at the field with thousands of other fans. For another good man date, you should consider going to a brewery. Most breweries will let you take a tour of the facility. You can see how the beer is made, then you and your bro can sample the beer in their bar at the end of the tour.
3. Watch your conversation.
Don't dwell on your job or on making money. Unless your friend works in the same industry, he is probably not going to be that interested in what you do 8 to 5. Have some other stories to tell.
Also, don't forget to listen! Nothing is more boring than a dude who talks about himself endlessly, except maybe a chick who talks about herself endlessly.
4. Paying is not mandatory.
The easiest solution is to agree to go Dutch treat in advance. However, there's nothing wrong with offering to pay and, if he lets you, taking care of the bill. Of course, you then have the right to ask him to pick it up next time.
If he wants to pay, you can argue that you want to - if you mean it. Your call.
5. Change it up next time.
Don't just meet for drinks after work every single time. Climb a rock wall, have a barbecue, get together for a jam session in the garage, if you can both play guitar.