One of the key turning points in the world of dating.
This remark, most often associated with a female person in a dating situation follows only after the "Would you like to come inside?" question is posed. The offer of coming inside can involve promises of coffee, a nightcap, or conversation. Once inside the home, a beverage of some sort is offered and accepted by the guest. It is at some point after this that "Would you mind if I slipped into something more comfortable?" is issued by the resident of the home.
This remark has a two-fold meaning. Slipping into something more comfortable is usually interpreted by the male person in the dating situation as meaning something soft, silky, sexy and revealing. He may consider it an overt sexual foreshadowing. However, one must keep an open mind and a calm eye. Something more comfortable may be taken in a literal sense. It may instead involve a baggy sweatshirt and sweatpants rather than a slinky negligee.
Many male persons will recoil at the appearance of said sweats. They are led to believe from years of intra-male conversation that the sweats mean an end to any extra-curricular activities. Perhaps they should instead realize that her appearance in such garb illustrates that she feels comfortable around him without being dressed to the nines. The hormonal male who feels strongly physically attracted to the woman in question will often fail to realize this important point.
Words of Warning: One should not attempt changing into something more comfortable in someone else's home. Unless you know someone well, going through their closets and dresser drawers for comfortable gear will be interpreted poorly. Also, when changing into something more comfortable in front of newly acquainted male associates who may feel romantic or sexual desires, women should remember that he is constantly looking for signs that "it is on." Of course, that puts you firmly in control of this portion of the dating experience... provided, of course, he is a gentleman.