[header] How to be a good wingman [title] Wing only for people who are roughly at your level. [step] Don't try to wing for someone who is significantly less appealing than you. These are harsh words, but they are true. 
You and your friend should be pretty similar in terms of your attractiveness, your outgoing nature, and your general appeal. Otherwise, the people you meet are likely to latch on to you, and your buddy will feel even worse.