When you get to the spot, start with introductions and light conversation to get things warmed up. You warm up before your kickboxing class, right? So, it's probably a good idea to do the same for this meeting. The first few minutes of small talk is also a good time for him to present your mom (and stepmother if it's a group effort) with the single rose or box of chocolate-covered pretzels he picked up along the way.
Keep the conversation casual but informative. Encourage him to talk about his background and share a little bit about himself (making sure to stay away from the pesky forbidden fruits). Help guide the conversation to topics like sports, news and current events. It's also OK to throw in some pop culture conversation about music and reality TV. Stay away from subject matters that could potentially ignite the flames, like who's right? The Dems or the Tea Party? If you do go there, keep it friendly if you find that he's disagreeing with them a lot.
If everything is going great, we're happy for you. If things are going downhill, it might be time to pull out that "Plan B" you have tucked away in your clutch. "What could go wrong?" you ask. Plenty. For starters, as time goes on, you may realize that your boyfriend and one of your parents mix together as well as oil and water. Or, your divorced parents get into a heated argument with each other. Or worse, someone spills red wine on your white pants. Remain calm and let your family know that the "date" is going to end early by thanking them for the company and either offering up an excuse to leave early or just bolting for the door. However, offer to pay your portion of the check, before saying goodnight.
If things do go well, the signs won't be hard to read. If your honey gets invited to the annual Thanksgiving dinner on the spot, or you mom doesn't wait for you to get home before she calls you on your cell to say she approves, it's safe to say that in their eyes, he's a keeper.