Dating Prospects In Sigil... *wry grin*

While none of my players have been masochistic enough to ask The Marauder out on a date yet in my campaign, one of them as of my last game session expressed interest in asking A'kin the Friendly Fiend out for a date.

Now, before you laugh, find it endearing or tell them to "RUUUUUN!" hear me out here. The PC is a lupinal member of the Ciphers who has, over the past 2 years (game time and real time) lapsed from NG to true neutral. In a sense she's a fallen celestial. A'kin of course may or may not be a redeemed fiend. He might just be crafty and subtle in his evil, or he may be similarly lapsed from NE to true neutral, or he might be fully redeemed and be just a generally nice guy.

In any event The Marauder loathes him and he's content to apologize for her, and his entire race's, actions half the time. So best guess what they're current or past relationship is. My game is no different in that you can make a dozen different guesses and have just as much evidence for all of them as to which is true or not.

This all started because the lupinal PC was going to graciously break up on friendly terms with her current NPC romantic interest for a number of reasons. He was mortal, CG, and honestly not powerful enough to be running around with her and her companions and not be a risk to them and himself. So she'll be on the dating market shortly.

The lupinal also was aware of Colcook, Shemeska's primary mirror holder tiefling, being an Argenach Rilmani. She wanted to get in touch with him to speak with him about the Rilmani race's potential involvement or knowledge of certain elements of the campaign's plot that I won't bother expanding upon here for brevity's sake. To that end she made an appointment to speak with The Marauder herself and inquired about literally renting out Colcook for an afternoon. The Marauder was amused, confused, and intrigued. So being what she is, she pried and prodded to find out the real story. The PC made up a story about wanting to learn poise and style, in imitation of The Marauder, the mirror would help, Colcook might have tips, blah blah blah. All sucking up to Shemmy's ego the entire time.

It almost worked except The Marauder insisted she be present for half the time, and that she'd be giving out tips. The appointed time arrived and she arrived with Colcook and her entourage of tieflings carrying boxes and bags of clothing, makeup, jewelry, etc. So for the next few hours The Marauder and the lupinal PC stuffed them selves away with Colcook and his mirror in a private room and talked fashion, social graces, poise, personal grooming, etc. The Marauder didn't do anything unseemly or evil, but she was clearly relishing the fact that the lupinal was terribly afraid that she would. So the paranoid lupinal got dressed up again and again and again, effectively playing dressup for a few hours with the 'loth. It was good advice though actually... she just had to endure feeling like a piece of meat a few times when she swore that she was getting checked out in the process of getting dressed. (Yes, I was merciless in that whole episode. I managed to make both PC and player alike paranoid, nervous, off guard and potentially squicked. But nothing actually was done... just the perceived threat of evil... bwahahaha)

Shemmy's price for this all however was to wear a dress of hers that would fit the lupinal, and do prancing over to A'kin's shop all dolled up. Just walk in, look around, wave and otherwise say nothing to him. The dress was just about skintight and threatening to pop for a description here... But the lupinal did so as the condition for getting to spend an hour or so in private with Colcook and his mirror.

That evening the PC walked over to A'kins getting hit on and catcalled by about everything male between the clerk's ward and the lower ward. And to some extent she enjoyed it. So she walks into A'kins shop, painted up, bejeweled, and wearing one of The Marauder's dresses. A'kin turns around at the jingle of the bell on the door and just stares openmouthed. She waves and he drops the vase he was holding to shatter into a hundred pieces. He just stammers and acts confused before she walks out.

Shortly thereafter one of the other PCs goes over to explain things to the Friendly Fiend himself and sits down for tea to discuss it all. A'kin had apparently thouht that Shemeska had walked in to taunt him or attempt to burn down his shop, again, just having shapechanged herself into the lupinal PC they both knew. After all, he's apparently seen that dress before, or The Marauder wearing it, and wasn't sure why else that the PC would walk into his shop all dolled up so uncharacteristically for her and wearing one of his archnemesis's evening gowns.

Well over tea, A'kin pops the question of whether the lupinal was currently seeing anyone. And things cannonballed from there. It looks very likely that the two of them may be dating shortly. This was not anticipated by me.

So... anyone have advice for me, or for the PCs here on how to handle this? *utterly unreadable grin*