I prefer going in alone. When you go in with your wing, you smack of all the others who did that.
Let me take a moment to explain two ways of going in; the BAD WAY and then the GOOD WAY.
First the BAD way:
You go into an FF 2set with your wing. your wing runs interference on the obstacle while you work the target. problem. if your wing cant keep it up, when the obstacle is disengaged she will think you have as little value as he. she will immediately drag the taget away, even if the target likes you.
The GOOD way:
You go in alone. work it like a 2set. neg the target, dhv to the obstacle (so the target can hear the spikes). then accomplishment intro your wing BEFORE he enters by saying, "I'm here with friends. In fact, Im going to introduce you to <name>, he's the one who <accomplishment>." then work your A2 material, get into A3, lock in and have your wing ONLY come in once you are locked in. And if he doesn't come around, use this as a reason to find him with two women on your arms (heating all sets witness to this display). ok now that he is in (he may have used, "Did you tell them about ..." and you will catch him up to speed on what routine he is on when he entered by saying, "Yeah ... and they said the dogs should be named Siskel & Ebert!") the wing should work the TARGET! what? thats right! he works the target ... FOR YOU! You arent getting along with her anyways (you will have put her through A2 haa, and A3 means she has to WORK to win you over hee) and you then isolate the obstacle! what? you cant isolate in a 2set. thats right, but its NOT a 2set is it? when your wing came in (or any other person) the 2set turned into a 3set. so you could isolate. in isolation, you will continue to speak VERY HIGHLY of your friend. You will do this for a specific reason: when he later engages her, you want it to stick. so your wing will, since he knows its your set (the one who opens the set leads the set), run an AI (accomplishment intro) for you. Now, because you entered alone (DHV), you made the obstacle accept you (DHV), you are hanging with a person of high social value (DHV), and that person thinks highly of you (DHV) giving her your background (DHV spiked). So now you can get the wing to speak to the obstacle and you can isolate the target who is now chock full of DHVs. Your wing will control the obstacle due to your AI of him to her. Your target will be attracted. now all you have to do is complete A3 and begin an isolated C1 with kino escalation and bang you are on your way to a new GF.