Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

What exactly would be the downside to going commando for the date?

If it was an enjoyable topic of conversation at the time, I can't imagine how he'd expect you to bundle up for this event, no?

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

Your connection at this point is "commando." To throw that away at this stage would be like telling him that his main theme means nothing to you. If you like him, stay with the connection. If you really like him, and want him to know it, emphasize the theme by going completely naked at some point.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

If you REEAAALLLY like him, you aren't going to fuck him until date 2 or 3, so the point should be moot.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

If you suck it, it won't matter.

TM

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

You see what I have to put up with on the politics board?

This is the conservative impulse at work. This is the man who joined the riot after "The Rites of Spring."

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

Not really. Even if she doesn't fuck him, it appears to be a topic of conversation, so if it comes up, she wants to be able to hold up her end of the conversation.

I vote for going commando again.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

You must have been with Bilmore when he first heard Monk.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

The above means he likes you. On your date do whatever you feel like- it doesn't matter. If the topic comes up and you aren't commando sidestep it- "Maybe you'll find out" or some such thing.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

First, I assume that's only an issue with pants or a long dress; do women really run around in shorts or skirts not wearing underwear on second dates?

How did the fact that you were both commando come up? Is there any chance that this guy is just looking for a quick and easy lay? Did you fuck him before? Some people (not me, but some) might think that a "first" date soon after no underwear was discussed might quickly lead to fucking and develop into a non-relationship sort of "fucking," if any future fucking is to occur.

If he seems like a guy you actually want to get involved with (I had "nice, normal guy you actually want to get involved with," but maybe that's not your thing), then consider whether the prior commando conversation and your current underwear decision tree are really compatible with that. I know plenty of guys who seem very nice and charming and are well-liked just enough to get laid, especially with recently-divorced women they perceive as eager to feed at the johnson trough, but it seems like you want to have more than that. His comment that you are destined to be together sounds like "I am destined to fuck you the next time we meet and I get you drunk," but maybe I am just cynical, or maybe I just evaluate the statements of other men as cynical and designed with ulterior motives. "Destined to be together" creeps me out in the first place.

So, anyway, maybe consider that issue. If that's not a worry, I don't think that it matters whether or not you wear underwear. It would intrigue me most if, if the topic came up again, you said something like "maybe you'll get the chance to find out" or something like that. But, then, most women with whom I am drinking and with whom I end up discussing our current underwear don't end up waiting for a second date to interrogate my commando, as it were.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

So what she wears is irrelevant - it's what she says to him that counts

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

Since paigow stole mine, I'll also offer up (if you're not) "No, somebody's got to take them off before I go to sleep tonight."

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

Why do I always have to be the voice of reason around this place? ABBA, your decision is very simple, and my wisdom is Solomon-like: Crotchless panties.

Jesus people, it's like you haven't learned a thing.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

You have to go commando. A, it's hot. B, if you do otherwise, you're giving him a form of the Heisman when he gets down there.

And just fuck him. Don't do the "wait" thing. That's for people who don't know what they're doing.

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

Photoshop king strikes again!!!

Outfit Advice -- Hey! It's the Fashion Board!!!!!!
 

Indeed! That's classic!