Given the increasing availability and importance of live chats in e-commerce, we examine when a salesperson should send a friend request to customers, moving it from a business to a friend relationship. We leverage the logistic regression to estimate the effectiveness of a salesperson's friend request on relationship and economic outcomes by using a large-scale archival data from an Asian luxury e-commerce firm. We find that (1) the friend request made in the middle or end of a conversation is more likely to be accepted than the one made in the beginning; (2) the more positive words used by salesperson, the less likely for customers to accept the friend request in the end than the one in the beginning, in line with the old saying-i.e., strike the iron while it is hot; and (3) the more standard answers used by salesperson to respond to customers' inquiries, the less likely for customers to accept the friend request in the middle or in the end than the one in the beginning, suggesting that superficial listening can't exchange for friendship. This study extends the current literature on the salesperson-customer relationship by investigating when the use of a friend request can influence customers' acceptance, satisfaction, and purchase decisions. We provide insights for retailers about how they can take advantage of friend request in the live chat context to increase customer satisfaction and sales volume.