Before I get into speeches and scripts, let's remember the stakes. Best case, one or both of these women say yes and you go on a date. Worst case, both say no, you do the good deed of letting two people know they're attractive and your delivery gets a little smoother with the next iteration. Even more important, you've proven to yourself that, after seven long years of domesticity, you still have the testicular fortitude to tackle one of the most fear-inducing romantic endeavors — asking a total stranger for a date. You are going old-school manly, my friend. The rest of us are hiding behind our computers.

Since I haven't been there to bear witness all the flirting, I'm going to give you several different scripts representing several different styles. Pick whichever suits the woman and the situation best, then alter it a bit to make it more natural. To help prevent verbal slip-ups, I've included examples of riffing-gone-wrong for each.

5) The Event Planner
GOOD: "I was thinking of checking out that radish festival you guys have posted over there on the Community Bulletin Board. Want to come with?"
BAD: I've made reservations at Fancy Von Upscales and purchased tickets to Pricey! The Broadway Show. Now all you have to do is say yes, m'lady."

As far as post-proposition logistics, paying with a credit card is the easiest way to help her learn your name. It also provides a handy spot for scribbling her phone number and email when you ask it. Or, ask for her number and email. Usually an email address will contain some form of the person's name. If it doesn't, time to dork out and just say: "Hey, I'm really sorry, I should know this by now. Can you tell me your name?"

One final note that hopefully will relax you: Asking someone out is more about mutual chemistry than the execution of the invitation. Look your best, try to have some measure of fun with it and leave the rest up to pheromones and fate.

Dear Reactive,

I've been dating online for years. While I usually take down my vagina shingle shortly after I start seeing someone, sometimes I've shown more hesitation. This can be for a variety of reasons: The other person hasn't taken down theirs yet and we're involved in an online-standoff. Could be I'm unsure about whether we're exclusive. Or I'm feeling restless and anxious about the boundaries (or lack thereof). Having an inbox full of messages from people expressing interest in you is incredibly ego-boosting. I don't care if ninety percent of them paint Civil War figurines and look like Gary Busey. It's nice to know someone wants you, even if your odds of reciprocating are a big, fat zero. Many of us, myself included, have a hard time eliminating it from our daily routine.

This is, of course, assuming he's not communicating with his cyber-constituents and actively contacting people. If he is, then a talk is in order. I won't weigh in on whether three months is a sufficient amount of time to extract a commitment from a guy in his thirties. Not because I'm stubborn, but because that stuff is so subjective. What seems like forever to some is a tiny blip to other people. Here's what matters most: your feelings. If all this vagueness is making you so uncomfortable that you're skulking around with anonymous log-ins, I don't think you should wait any longer. You're liable to have a breakdown in which you spew all sorts of accusations and ultimatums, all of them based on incomplete knowledge. You're basically just guessing at his feelings.

Find a time when you're both feeling chill — in the car on the way home from a show, or polishing off some take-out in front of the TV — and start asking questions. "How are you feeling about this relationship and the way it's been going? Do you still see other people?" If yes, then, "How much longer do you see that continuing? What would it take to be exclusive, or is that not something that fits in with your plans right now?"

Keep it open-ended to start. If that goes well and he doesn't get super-defensive, then go into specifics: "I see you're on the dating site quite a bit. What's that about? Do the people you talk to know that you're seeing somebody?" Hopefully his answers will give you a better indication of his current thinking. Watch out for sweeping declarations that go against his current behavior. You're better off with an honest guy who expresses his reservations than someone who tells you what he thinks you want to hear. The latter is likely to cheat down the line.