There are only two reasons one needs a wingman; The first reason one needs a wingman is to have someone to drive the car home in the event one decides to go home with the girl in "her" ride. If one decides to take the girl home instead, the wingman is on his own for transporatation home.
The second (and most important) reason one might have a wingman is to "have your back" in the event that there may be a jealous boyfriend, husband, friend, co-worker, wanker, etc who might happen to try to cock block you from seducing your intended partner, all while he (and usually his loser buddies) tries to cock block you all hopped up on Budweiser or Coor's and testosterone (You never know when you might be faced with your very own "Viet Nam Vet Story' to tell
).
Otherwise tell Isaiah to "man the fuck up" and get his ownself laid. Grow a pair, and stop being so intimated. He needs a wingman? No wonder he can't get laid. The reason I was so successful with women while I actively fueled my sexual addiction problem was I would ALWAYS go after the most beautiful woman in the place. Tell him to be himself, be funny, be direct, and put all of his attention on her. Seduce her.
Tell Isaiah, the best way to "seduce" a woman is to totally focus on her in the club. Tone out the music, the crowd, and everything else- and focus only on her. Study her from across the room for a short while. Study the arch of her back and visually follow the line around her buttocks and down her legs. Study her smile, her jawline, the way she moves, the way she walks, her laugh, the way she flips her hair out of her face. Watch her body language for cues. Then go straight in for the kill while the sharks are still posturing and circling from afar. She knows the sharks are there. She can feel them. She can smell their sweat, and cologne. The air is thick with their testosterone. She's busy looking out for their fins and fending off the sharks, and she's not even aware that the "vampire" has been studying her until it's too late. Once you make your move, be yourself. Be talkative, be flirty, be confident and seduce her. She wants to be seduced, not "picked up". If you do it right, it's a foregone conclusion she'll go home with you. Don't be creepy, and don't be shark. Sharks go home with anyone, and usually alone.
The art of seduction comes easily for some people. It's much harder for others because they spend enormous amounts of time avoiding the opposite sex because of fear of rejection or they can't get past their own hangups. Still there are some of us who are addicted to the seduction, and it winds up controlling your life, and ultimately not in a good way either. If the end game for your friend is getting laid, then he should learn to do it right, or not waste his time.
I should charge for this stuff.