Ideas for romantic complications

[Anymage]

One of my players is running a bit of a womanizer. I figure every now and then, it'll be fun to mess with him and throw a bit of a curveball with that specific barmaid. I'm just looking to do something a little different from the usual standbys; save vs. crotchrot is overdone, coming back nine months later to find that you're a daddy involves too long time scales, and having her turn out to be some sort of monster feels more punitive than I like. So what might be some good low-key complications to throw his way?

[Koo Rehtorb]

She thinks they're dating now and expects him to stay here.
Daddy catches them in the act and now he and his buddies are trying to impose a crossbow wedding on them.
She's a con artist, doses him with knockout poison in a drink, and tries to steal his stuff once he's in bed and passed out.
She's a con artist, and her buddies (large men with large clubs) are hiding in the closet to beat whatever sucker she lands unconscious once he's in a vulnerable position alone and out of armour.
She's married. Husband's not happy.
Weird local laws, they're now considered legally married.
The bed is ACTUALLY A MIMIC!!!
He's drunk and doesn't realize until clothes comes off that she's actually a feminine looking dude.

[Recherché]

Turns out being a wereplatypus is an STD

[mucat]

She wants to know everything about the PC's adventures. Turns out she's a bard, and the songs and stories she invents might make or break the party's local reputation for a long time to come.

She wants to know everything about the PC's adventures. Turns out she's a rival adventurer, hoping to poach quest hooks from the party.

She wants to know everything about the PC's adventures. Turns out she's just curious.

She's a con artist and is running a con on another mark altogether. It Goes Horribly Right, and some very dangerous people now want to recover what she stole, which is far more valuable/important than she anticipated. The marks assume that anyone recently seen with her, such as the PC, are in on the con, and apply pressure accordingly.

She has, like, twelve cats.

She talks in her sleep, and mentions a name the PC cannot possibly ignore.

The night was enjoyable, but in the morning she's gone. Like, seriously gone without a trace, and the PC was the last one seen with her. As suspicious eyes turn their way, the party must either solve the mystery or skip town in a hurry.

Her spouse comes home unexpectedly, forcing to PC into a desperate and precarious hiding spot. When the PC hears the spouse's voice, it is terribly familiar.

She has, like, twelve cats. One is not what it seems.

[False God]

Many of mucat's suggestions would work well to be combined into a single character, an in-depth complication that adds momentary humor to the situation, trouble for the womanizer, but also ties back in to the greater story so....

She's a skilled con artist adventurer running a long-con on another mark, and the PC looks like some easy side fun to purloin some recent quest loot or pick up rumors on where a great treasure or adventure may be. Her Other Mark comes home while she's having her fun with the PC, the voice recognized by the PC as someone relevant to them (someone he can't just stab but also can't get caught by). The Other Mark has taken something (which is what "Connie" is after) and so the people that are after him are now looking for her and by extension everyone she's been involved with recently.

There's a fight, and when PC comes out of the cupboard Other Mark is dead (with the PC's knife!) the McGuffin is missing, Connie is gone and everyone knows where PC was last night....

Connie has of course, run off to join her adventuring party, who are probably a bunch of ruthless mercenary types.

---
You now not only have a complication, but a very legit new element to further the game!

[Vaern]

She wants to know everything about the PC's adventures. Turns out she's a bard, and the songs and stories she invents might make or break the party's local reputation for a long time to come.

She wants to know everything about the PC's adventures. Turns out she's a rival adventurer, hoping to poach quest hooks from the party.

She wants to know everything about the PC's adventures. Turns out she's just curious.

She wants to know everything about the PC's adventures. Turns out she's also sleeping with a major villain, and sharing valuable information about the PC and his travels.

She wants to know everything about the PC's adventures. Turns out she is a major villain, and is collecting valuable information about the PC and his travels for her own benefit.

She insists on coming along for an adventure to see what it's like for herself and becomes a liability that the party (or at least that particular character) must keep out of danger.

Some sort of villain, perhaps a warlock who is known to be the "king" of an exclusively female tribe of thieves or maybe some sort of giant fire-breathing turtle with a spiky shell, strolls through the town and abducts the PC's love interest.

Turns out she's really only pretending to be interested in the PC to get close to the rest of the party, in order to spend time with the adventurer that she really has a thing for.

The night was enjoyable. In the morning, he wakes up to find that she has made him breakfast. It would be rude to turn her down. Once he has eaten, she insists that he join her in strolling around town and shows him a number of local landmarks. Of course, it's not gentlemanly to just eat a home-cooked meal and immediately skip out on her, so he goes for a walk. Later she suggests plans for the weekend. By now he's in way too deep to back out. While they're out at the theatre or whatever it is kids do these days, the tavern is attacked and robbed. The owner is killed in a scuffle. When they get back and receive this news, the party gains a quest to track down the thieves. When all of this is over, the barmaid finds that the tavern has been left to her. She asks the PC to help her keep the bar afloat, as she can't perform all of her usual labor while also tending to all of the previous owner's old responsibilities. She insists that it'll only be for a short while, until she can find a new employee or two to pick up the slack. Turns out the PC is pretty decent at the new job. The barmaid can't find anyone quite as good as him. Plus, he's working practically for free at the moment, and as long as he's stuck here and not out adventuring she has him all to herself... He's trapped. He begrudgingly admits his retirement from his career as an adventurer to work at the bar full-time. The player must now roll a new character. He should have just skipped out on that breakfast...

[Jay R]

A seven year old girl who (falsely) believes he's her father. When he's just getting along well with the barmaid is a great time for a small child to walk in and say, "Daddy, when are you coming back to Mommy and me?"

Or perhaps, "My dolly broke. Can you fix her, Daddy?"

[King of Nowhere]

She wants to know everything about the PC's adventures. Turns out she's also sleeping with a major villain, and sharing valuable information about the PC and his travels.

she admits that, and claims she's selling information on the villain. turns out she's selling informations to both the party and the villain. and she has a weird sense of honor in that she sees nothing wrong with selling information to both, but her information is genuine
now you no longer have to worry on how to drop plot information on the party, or how to justify the villain setting up ambushes at the worst times

[Kardwill]

...
She's a con artist, doses him with knockout poison in a drink, and tries to steal his stuff once he's in bed and passed out.
She's a con artist, and her buddies (large men with large clubs) are hiding in the closet to beat whatever sucker she lands unconscious once he's in a vulnerable position alone and out of armour.
She's married. Husband's not happy.
Weird local laws, they're now considered legally married.
...

"So, in a nutshell, you've been dating Saffron. Roll Save against impending doom"

[Zhorn]

Turns out she's a bard and you were HER one night stand. You awake in the morning with a note thanking you for the time... but you recognise it as a calling card of a practised nail'n'bailer, and the sentiment strikes you as a hollow gesture... Sitting there in the bed you feel a creeping sensation wash over you as you realise you meant nothing to them in the long run... Just a pretty face to be forgotten and discarded. You never seduced them... they seduced you, and now you're left behind feeling used, alone and unloved.

[Max_Killjoy]

She insists on coming along for an adventure to see what it's like for herself and becomes a liability that the party (or at least that particular character) must keep out of danger.

IMO, this is one that's actually been over-done, at least IME.

[Duff]

The baroness is delighted to see last night's playmate appear in court asking for a favor she can easily give.
Trouble is, the Baroness' girlfriend is delighted to see yesterday afternoon's playmate..

[Malphegor]

She's actually a changeling, and has actually been ALL of the character's romantic partners, under a different disguise each time.

[Max_Killjoy]

The baroness is delighted to see last night's playmate appear in court asking for a favor she can easily give.
Trouble is, the Baroness' girlfriend is delighted to see yesterday afternoon's playmate.

Girl friend, or girlfriend?

She's actually a changeling, and has actually been ALL of the character's romantic partners, under a different disguise each time.

He'll never live that down, but he might as well marry her... how will he ever trust anyone else to not actually be her?

[NNescio]

Dragon shows up with army of kobold lawyers demanding child support. By draconian (heh) standards.

[FaerieGodfather]

Having the one-night-stand turn out to be a horrifying monster is kinda played out... assuming the monster is hostile and wants to eat the PC, before or after their assignation.

I've never seen the one-night-stand turn out to be a horrifying monster who is genuinely in love with the PC. Not jealous, not possessive, just deep-in-their-bones Chaotic Evil, immensely powerful, and the PC's success and happiness are the most important things in their life.

[Grey Guard]

There's been some excellent suggestions so far in this thread. I feel like I don't have much to add.

She's actually a succubus. She has no intention on hurting the player, and genuinely likes him. She's still a Chaotic Evil exemplar, so that 'like' might manifest in uncomfortable ways.

She's actually a changeling, and has actually been ALL of the character's romantic partners, under a different disguise each time.

This made me chuckle a bit. Love it.

[TrashTrash]

*cracks knuckles* Oh, my time has come.

- Turns out the girl is the ex-girlfriend of some other NPC he's seduced, here to ask about their ex's relationship-ending fling. Crying is a good thing to throw in there.

- The girl turns out to be stalking the PC, but this is only revealed after the deed is done.

- The girl insists on introducing him to her parents beforehand, which will delay their rendezvous by about four hours. Will he still do it?

- She accidentally gives him food poisoning from rushing his order out to see him sooner. (Bonus if said dude has a low CON score)

- She begins aggressively yet genuinely flirting with anyone and everyone in the party EXCEPT him.

- She brutally insults him in rhyming verse, but is also coming on to him at the exact same time. (Mixed signals are fun, aren't they?)

- The minute they walk into a private room, she forgets what they're doing and starts cleaning up instead.

- She turns out to be several ducks in a cloak.

- She begins sending him "anniversary" presents, the first one arriving at one week post-fling, the second at 1 month, so on and so forth, until finally at about six months in she tries to meet up again and get married. Have fun with that one.

- She greatly misunderstands what it means to sleep with someone and crashes out on his bed, snoring like a werebear.

- She turns out to be a twin, he approaches the wring twin and gets backhanded for his comments. Hard.

- She will not stop sending "free" drinks to his table. He finds out when the party leaves that he owes the bar a LOT of money, since she charged him for both the drinks and the one night stand.

- She has a life-threatening allergic reaction to something he ate when they kiss.

- Turns out, she's not good at keeping her lunch down when she's nervous. Laundry day for everyone!

[Duff]

Girl friend, or girlfriend?

Yes!
Does he know? Don't tell him, just play it. Let the character (and maybe player) squirm for a few minutes as he realises his day is going to get more difficult

[Phhase]

*cracks knuckles* Oh, my time has come.

-Excellent Suggestions-

PPFFFF. I like the way you think!

A few of my own!

-The barmaid is a werecreature, and it's the full moon! Hope you're a furry!

-ANYTHING involving a False Hydra (Look it up)

-She's into the weird stuff.

-She has some sort of sorcerous bloodline, and this encounter awakens it, causing (magical effect, possibly transference to another plane. Could be a whole subplot).

-Turns out, she's an adventurer! She just hasn't had any work for a while. Will gladly join the group as an NPC and the player's girlfriend (with all the responsibility that implies).

-The barmaid is a cult member and tries to indoctrinate the player.

-Nothing happens. Later on, an enemy necromancer sends a hauntingly familiar undead after them...

-Turn out, she slept with the player on a bet.

-Not only was she not human, but the player sired a half-offspring, which later on reaches out to the player, desperate because its mother abandoned it.

-Either deliberately or by complete accident, the barmaid poisons the player with some sort of slow-acting poison or effect with interesting consequences.

-The player contracts a curse that is most easily passed off by sleeping with someone else. Bonus points if the big bad is the original creator of the curse.

-The barmaid slips a mickey to the player. Right when he's about to get it on, he realizes he's impotent! How embarrassing...

-Deliberately beds another player out of pure spite.

[Elvensilver]

Some more ore less benign meetings

After the night, she tags along for a few hours, then decides to save any pets the party may own - if you retrieve them, you see:

She has, like, twelve cats.

and a lot of other pets. You only ever was a mean to her, to "free" your animals.

She's actually a medical/clerical professional and diagnoses you with a rare disease which will soon become unpleasant if you do not treat it now. Or she's just scamming you.

You are being invited to a local cult meeting.

She slept with you to break up with her boyfriend, and won't stop trashtalking him.

She did it as a dare - or did not do it, but asks you to lie for her- and parades you around to proof her deed.

She's from another culture, and regulary makes inapropriate offerings to animal Gods (like all your hair, after you fell asleep)/ she pays you afterwards - or if not satisfied, demands a pay.

She's a polymorphed non-humanoid on a research trip.

She's really forgetful, almost suffering from dementia, and can't remember you on the next day. Or she can't remember faces.

She starts speaking in Tongues, revealing a forecast considering you.

She absolutly understands why you can't be together, but persistently tries to play match-maker to find you a girlfriend.

[TrashTrash]

Thought of a few more over breakfast.

- He never quite sees her face all the way, whether because she wears a veil or because her hair is in the way, but once he starts to act all romantic and sweeps her hair behind her ear, he discovers that she's his cousin whom he hasn't seen in over a decade. Whoops.

- She starts talking about how she's never met a guy like him, how she'd be thrilled to have him come up with her, how she can't wait for their meeting. When he shows up, she has knives everywhere and some odd discoloration on the floor. (Spoiler alert: It's from blood.) She starts talking about spiders, how beautiful their handiwork is. How wonderful their form is, their instinct, their strength. (Spoiler alert 2: She's gonna try to kill him after they sleep together. Like a spider.)

- In a wacky series of events, while they're in the act they accidentally set the whole place on fire. They do say passion is a flame...

- Oops, looks like she's pulling a Bachelorette. Seven other dudes show up at the same place they're supposed to get together. Looks like you have to fight for her affections!

- Hey, remember that other, totally ripped NPC I definitely mentioned earlier? Yeah. That's her brother and he is NOT happy with your little rendezvous. Roll Initiative!

- Right before the act, she pops something into her mouth. She starts hallucinating that he's a dog about 2 minutes later and he has to cancel the appointment until they can deal with the side effects of whatever she's tripping on.

- She's got legs for days... but they're goat legs. Have fun with that.

[darkrose50]

She is actually a powerful being (a demon princess) on a vacation for one-human-lifetime, and had her memory blocked for the authentic human experience. Several of her suitors, are various other powerful beings who know the truth, and want to take the chance that she might fall for them when her memories return (political marriages to advance their status). The suitors are not at all pleased that this upstart is stealing her heart. The suitors also know that if they ruin her vacation that it would negatively effect the standing of their families. So they can't just go gonzo with death and destruction, or they will ruin the game. In fact it would be best for them to "stay in character". It is important for them to not impact the princesses authentic human experience as much as otherwise possible.

Bonus points if she shows up while fighting a demon, and the party freaks out that they need to keep her safe. When the demon is about to attack her, he stops, greets her politely, and says "I did not know that these mortals were with you. I apologize. Please enjoy yourself" and leaves.

AND/OR

Cultists cast a spell to find the "one that is most pure" to sacrifice. They kidnap the barmaid. The big fight is against the cult. The cult times the ritual. The heroes show up. The same demon from before shows up (perhaps in disguise), tells the party that "I am here to help", and kills all the cultists. He then says to the barmaid "I apologize for my insolence. I will insure accounting completes a complete audit of this spheres infernal allotment" and then vanishes.

Hopefully everyone panics.

-----

I would frame this as a cosmic loophole. She is reincarnated into a human by birth. She does not detect as evil, because she is not evil. Her "evil" is blocked up someplace with her memories. She will once again be evil when her evil mojo and memories return, and this is set to be at the end of her human lifespan.

Perhaps a diviner can tell that she is reincarnated evil, and will reincarnate into evil. Perhaps the diviner can tell that when she dies evil will gain power. Perhaps a high level divine caster can tell that there is an unusual and complete absence of evil in her, and that is simply unheard of.