Dropping the S Bomb

I have a friend in his fifties who has been dating for about thirty years now. He’s a smart, interesting and funny guy who has never been married, and could reasonably be known as a serial monogamist. Once, in a conversation about dating he mentioned that he has started telling women that he goes to shul every week in his first conversation with them, just to save time. There are apparently a lot of Jewish women out there with no interest in dating a guy who’s big on going to synagogue. And in my own experience I’ve found that it can be incredibly delicate, especially within the Jewish community, to explain to a friend or significant other, that you want to go to shul.

So here’s my question: when do you drop the S bomb? When do you say, “Hey, I’m gonna get up tomorrow morning to go to shul?” or “Any interest in coming to Kabbalat Shabbat with me?” If you know you’re dating someone with religious views that are very similar to your own, or who you met at shul, then it’s probably not going to be a big concern. But if, like most people, you’re dating someone with a slightly different take on religiosity than you, when do you start to broach the subject? When do you own up to being as observant or as unobservant as you really are?