So here’s a topic which I’m pondering as something a new character might indulge in at bit.
I hope I’m reasonably clueful as to recognising when another party starts things (at least IC 
), or the signs of when this is unwanted. But any common sense safety tips would be welcome.
So what do you find enjoyable when being flirted with as your character IC? What makes you feel at ease doing this with another player?
Ask OC first, either they or their partner might not be happy about this occuring.
From experience, the top thing has been the other player being clear about the difference between their character’s IC behaviour and attitudes (whether that’s suave flirting, awkward flirting, or whatever), and the player’s own OC behaviour and attitudes, which I find best when it’s friendly and/or polite and obviously not flirty. I’ve had good fun when our attitudes towards our characters have been “lol okay our characters are totally useless at this aren’t they”.
(Keeping clean IC and OOC separation of how you feel about a character and their player is something I find really important for maintaining my keen and my even-keeled-ness at events.)
As a counterpoint to this: I think it’s reasonable to do a bit of IC light flirting without an initial prompt, but if you do it for more than a little while and/or the other character seems to reciprocate, it’s a good idea to have a quick OC chat about boundaries, what sort of thing they’re okay with, and err on the side of doing less rather than more if you’re not sure.
(I am a bit twitchy about “their partner might not be okay with this occurring” - whether your partner is comfortable with you roleplaying romance with other people is a reasonable thing, but also if someone is not comfortable with even seeing other people flirt with their partner even if the partner does nothing to reciprocate, that feels like perhaps they need to figure out why they have that discomfort, rather than making it their partner’s problem. But I’ve probably read too much into what you said. )
Obviously, personal opinion disclaimer here but…
I am more comfortable when IC flirting is initiated based on my deeds, opinions or reputation rather than my appearance.
In a tabletop, I can happily play someone physically completely unlike me. In larp, with some variation of costume and makeup, I look like me. Because of that, especially if it’s someone I don’t know at all OC, comments on my physical appearance can be uncomfortable (with exceptions on things that are obviously IC, like lineage markings!)
Came here to say this, IC flirting works best if it’s based IC.
Personally, im terrible with flirting OC… i simply lack the hardskill. I dont take offence, or have any self image issues. Im just oblivious.
I also get a bit uncomfortable with touching, specifically when i don’t know the intent of it. Combat, i’m ok with all touching. Medical RP… sure. Hugging… what hug do i use? which one is appropriate for the circumstance. Do i do the kiss cheek thing first? if i hug wrong does it look like i’m flrting when i don’t want to. Is this me being awkward, or my character. #socialoverthinker
In terms of the partner thing. I, wierdly would be ok with people flirting with my partner. If she was 110% ok with it occurring. But i would feel OC uncomfortable if i was in a similar position, if she was ok with it or not (somebody IC hitting on me while she was there. )
For me, im open to the concept of it. But for other systems, i tend to leave it in downtime or froth.
I think i agree with people above. Best checking OC first and be ready for somebody, partner or the player to put an abrupt OC stop to it.
So what makes me comfortable?
It helps if the flirter is in the right place to be doing the flirting. If you (generic you, not Mark!) are OC lonely and trying to find a partner, probably now is not the time to be playing with ic romance. If your self esteem is low and you are relying on your character’s romantic life to feel good about yourself, you probably want to be careful because the path of ic love may not run smooth and those rejections and losses can hurt like anything out of character. Bleed is real! Talk out of character about how you will handle it.
With that said, what makes me actually keen about flirting? Stuff that is ic inappropriate or scandalous, where there is drama to be had. Road blocks. Mutual support. Little details that make stuff real. The potential for heartbreak.
Echoing what others have said… OC communication is a must and keep everything firmly grounded in IC.
Golden rule: As with real life flirting, at the first sign either party is feeling uncomfortable then disengage. Then if necessary apologise.
An easy way to flirt is to be complementary. Say nice things about the person you are IC flirting with, but make sure they are IC comments. Flattery rather than Lechery is the way to go here, “Who wouldn’t want to spend the evening with the finest swordswoman in the Empire?” and a cheeky wink is always a better bet than a generic comment about specific body parts.
Obviously if it’s someone you know OC and can pre-arrange or discuss limits with then this rule can be relaxed a bit, but generally keep it light. Heavy handed IC flirting is awkward at best and downright creepy at worst.
Final thought. Having both played an IC flirt and been heavily flirted at IC (admittedly because the character had something of a reputation by that point) I’ve found the most successful flirting comes with no expectations.
To clarify, the aim is to make any flirting incidental and secondary to whatever your character is doing. Flirt outrageously while doing something else and do not on any account stop and wait for a response. Carry on with the sword fight / dancing/ inquisition or whatever else you happen to be doing so that the other player can pick it up and run with it, or roll their eyes and ignore it at their discretion. By making sure that decision is clearly with the other player (reference the golden rule) you go a long way to just playing a flirt, and not playing a creepy stalker.
Personally, what I find is that I tend to be friends with people OC first - so know how they are with flirting - and then that leads to flirting IC. But at the end of the day, just flirt as you would OC, and use normal visual cues to see if they are not interested.
If your character has a crush on their character, I reccommend speaking to them OC if you plan on trying to persue a relationship, but like I said before, flirting with someone IC is just like flirting OC, if someone is not into it you can tell, and you stop. And they know its within their right to break character to say “can you stop?”, but yeah .. just use normal visual cues. If they look uncomfortable stop, if you think they might be uncomfortable, break character to double check that it might be IC uncomfortable or OC uncomfortable.
Generally, as with real life, its all about communication and body language cues.
Good luck! (And feel free to flirt with my character Sneery of the Wyverns Watch in Wintermark - I tend to find it hilarious and depending how drunk Sneery is, Sneery tends to find it good fun too!)
Seconding the point about disengaging as soon as someone seems uncomfortable. It is very difficult to distinguish IC rejection but OOC wanting you to carry on trying from OOC not wanting to roleplay this - ALWAYS assume the latter. If by “no” they mean “I want to roleplay hard to get” then they should tell you that. Asking them could make them feel under pressure to say “yes, this is fine” when actually they’re not fine.
My usual approach is to be flirty, but with absolutely minimal physical contact. Then contact them between events and ask a bunch of explicit questions like:
Personal story: I once made someone uncomfortable at Empire because he thought I actually wanted to sleep with him. Once he made this clear, we dropped OC and I explained no, I was just looking for purely downtime shenanigans. I felt awkward that I’d not clarified this to him sooner, but was all sorted with a couple of OC sentences and we dropped back into rp-ing very quickly.
Making someone uncomfortable doesn’t have to be a big deal - apologise briefly and ask them how they would you prefer you back off, then back off. If you are routinely making people uncomfortable, consider sorting things OC first and tone down IC behavior in game with people you don’t know. Good signals of discomfort to watch out for: person leans away from contact, crossed arms, person tries to leave conversation with you asap, person avoids looking at you.
Another good thing to consider: flirt with people in public not private (unless you know them OC well that they will be comfortable with this), in particular don’t flirt with people you don’t know alone in their tent while blocking the only exit and don’t follow those people back to their tents late at night unless they explicitly ask/agree to it.
Also, Urizen is the BEST nation for ballgowning (may be biased). You can have scandalous public displays of affection consisting of things like putting your hand on their shoulder. Dawn is pretty good as well as a single red rose says far more than any physical action someone might never want to engage in IC. But still make sure the other party is OK roleplaying it.
As one of my now-dead characters, an IC relationship happened with outrageous innuendo, leading to a brief OC aside in which we discussed the terms of the RP involved in the IC relationship and how we were going to follow it up.
This 20-second OC conversation enabled us to continue on mutually agreed ground to a few really nice moments and culminated in us arranging a date a year later, to finally actually get to know each other before, guess what, I popped it in an afternoon skirmish shortly beforehand. Trauma and sadness all around, everybody wins!