The One With The Birth Mother - S10-E9
Plot hole: David Schwimmer is 6'2" tall and Jennifer Aniston is 5'6". There is no way that clothes that fit Rachel would also fit Ross. When he puts on the clothes that Rachel bought it's obviously not Rachel's size. If it really were, it would be a lot tighter and shorter (Ross could probably wear it belly free).
Answer: Usually by the seventh night of Hanukkah you don't know what to get the other person, and you will probably resort to getting the other person something insignificant. Chandler is basically saying that the pen is a stupid gift.