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(I'm not sure if this belongs here or in interpersonal.SE; I decided to post here because I hope that others may have first- or second-hand experience.)

The premise is simple: in my weekly 5e campaign, I've grown fond of one of my players. Obviously, it's bad form to flirt while the campaign is running, so I've restrained myself there. I want to ask her out, but I'm not ready to put my campaign on the line for a date (I'm not sure if that's sad, or dedicated).

What experience have you had with starting relationships "over the table top"? Is it bad form for the DM to date one of his players? Is the outcome inevitably bad?

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tl;dr: Tread carefully and don't be creepy.

(I think this belongs more on interpersonal.SE, and relatedly recommend reading this, but I also realized I have relevant experience so I'm going to answer it here as best I can.)

If my username isn't clear, I'm female :) and I've been in this situation from a couple of different angles. Way back when I started playing D&D as a high school freshman, I played with a group of mostly senior boys (it was a small school; having friends across grade levels was normal). One of those boys developed a "crush" on me that rapidly turned creepy, to the point where I considered getting a restraining order. Fortunately he left for college before it became an issue, but our D&D group was irrevocably destroyed. The interpersonal byplay from him trying to put the moves on me was unpleasant for our mutual friends, who felt stuck in the middle or forced to pick sides. And obviously I wanted nothing to do with someone who refused to take "no" for an answer.

Several years later, when I was in college myself, I played with a different group of friends. We gamed under one DM for a year or so, during which time one of the other players and I grew close. He asked me out not long after I started a campaign of my own, and almost a decade later, we're still together.

So the answer for you is a resounding "It depends". The factors it depends on:

  1. You being willing to gracefully and permanently accept a "no" from her

  2. Her reaction to being asked out, and whether or not she has any interest in pursuing a relationship with you

  3. Whether you two hit it off, and if so, for how long (if your relationship outlasts the game, that's fine, but if you have a messy breakup mid-campaign, what will your plan be to handle it?)

  4. Whether you and she are both mature enough to keep a relationship out of the game (no playing favorites, no/limited flirting at the table, etc)

  5. The reactions of your other players, and whether or not they're comfortable with a DM/player relationship at the table (which itself largely depends on #4)

And possibly more. Asking out one of your players is a big risk! It might end well, and it might end badly. Ultimately it comes down to, can you, and she, gracefully and maturely handle whatever result comes from asking her out?

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From your question it seems that you've had an interest in her for a while, so it is unlikely that it will go away.

The thing with feelings is that it doesn't work to suppress them. Sooner or later, you have to face them in one form or the other.

The other thing about life is that in general we are more sorry about things that we didn't do than things that we did, even if they turned sour.

So the only reasonable option, from the information you have provided, is to ask her out. You should definitely do this away from the game, and by that I mean not only after a game, but really away from it. Where else do you meet her? Ask her there.

If she refuses, you need to do the following:

  • explicitly tell her that you accept it
  • explicitly tell her that she is still welcome at the game, of course
  • make absolutely no further moves on her

If she changes her mind, it is now her responsibility to tell you, without ambiguity.

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I am also torn between referring to interpersonal.SE and answering here, but there are some gaming-specific aspects, so I'll answer here.

(And please understand I'm writing this answer not just to you personally, but to a future audience of everyone who sees the the question and reads this answer.)

1) Be a gentleperson from start to finish

...whether the finish is in five minutes or fifty years. This is the same advice you'd get for any relationship: Don't be a creep, don't be a stalker, don't refuse to take no for an answer, etc.

2) Dating and gaming does not inevitably lead to bad outcomes

I've gamed with spousal pairs as players, I've gamed with spousal pairs as the GMs, I've gamed with couples dating through games, I've introduced a girlfriend to gaming, I've seen others do the same for their significant others, etc. I cannot specifically recall a GM asking a player out for the first time during the tenure of a game, but I'm surprised by that fact.

The overwhelming majority of these situations, including mine, have been positive, at least from my vantage point. And while horror stories abound, the worst I have ever personally experienced have been fairly mild. ("Really, buddy? +5 Holy Avenger for the third level paladin?")

3) But your concerns are real and they are valid

Because the thing is, there is a power imbalance between a GM and a player. It's not a huge thing in the context of the real world, because it is a game. But it is a potentially huge thing in the context of a game because one of your is in charge and the other one isn't.

This means two things, to my mind:

First, see 1) above: Be a gentleperson. That means taking extreme pains not to link the date (or the request) to the game in any way.

Second, I won't lie: If she says yes and you end up a couple, this can be a source of stress as you struggle to maintain fairness in the game without over-reacting, and also keep a healthy and happy relationship. But I can assure you it is not insurmountable.

And maybe one day, you two will be one of those adorable spousal-pair GMs!

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As the other answers specify: don't be creepy and no means no.

If you only see this player during your weekly game, it's probably a good idea to get to know her better. You can invite all your players to another event.

"I'm going to this club/geek bar/Comic Con/cat conference, would you guys like to come as well?"

On this outing you can get to know her better and talk about non D&D-related stuff. Make sure you talk to all your players and don't just focus on her. If you guys hit it off you can ask her to meet up another time.

And as the other answers state, the consequences can vary:

  • You might go on a date but not hit it off
  • She might say "no" and quit the game
  • She might say "no", but want to continue the game
  • You might become a couple for a short while
  • You might become a couple for a long time

In order to keep the game fun, it's very important you make sure the probability of her saying "yes" is rather high.

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