Will and Grace dread a dinner date with married friends Rob and Ellen who likely called the meeting to announce Ellen is pregnant yet again, but when the couple reveals that they are separated and loving it, Grace gets depressed. She's quickly distracted however when Will's cop ex-boyfriend, Vince, approaches their table as their server. Ignoring Rob and Ellen's big news, Will and Grace discuss how Vince must have gone off the deep end and quit the force after splitting with Will, and Vince's request to switch table assignments seems to confirm their thoughts. Elsewhere, Jack decides he needs to spice up "JackTalk" by pulling an Oprah and helping his fan, Tommy Shields, come out of the closet. Jack and Karen setup a bowling alley meeting with Tommy when Karen is recruited to join a woman's league game as an emergency fill-in.