Quote Originally Posted by VoxRationis View Post
To be clear, I'm not planning on asking her to have sex. I mentioned that I was concerned about interpretation as sexual harassment because laws and policies regarding said tend to be sensitive and based primarily on the subjective experience of the accuser,* so in a hypothetical world where she overreacts, I might not be on solid ground. My current (nebulous) plans for the date are mostly revolving around chatting over drinks or dinner and maybe playing some games or some other activity of that ilk.


Spoiler: *
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Which, to be clear again, isn't to belittle or downplay the seriousness of genuine sexual harassment. It's just that a lot of policies on the subject are written such that politely asking for a date and respectfully accepting whatever answer is given is technically as much in violation of the policy as many far more objectionable actions. My workplace's official sexual harassment policy, as defined in the employee handbook, has a line about "unwanted advances," which is incredibly broad and is notable in that one can't know whether certain advances (like asking someone on a date) are wanted before making them.
The fact that you're concerned about these things makes me think that you're not going to be too much at risk of it being interpreted as such. The people who are most at risk of that are those who ignore the reality of sexual harassment in the first place.

Remain watchful of that, make sure you don't get creepy or stalker-ish, and back off if she seems uncomfortable, and you should be ok.

Back to the actual issue at hand, though...

I've known plenty of people who met through work, or work together after they met, or whatever. It can be fine. The fact that there's no power imbalance is key. The fact that you're actually in different departments is even better.

Your ex is right that in an ideal situation you'd be able to arrange some group hangouts where you can get to know this person better. If you can set something up (say, inviting a bunch of work friends over for a board game afternoon on your day off) then by all means do so.

That said, it seems like this isn't the ideal situation, and doing that may be difficult.

If that's the case, then feel free to just ask her. (You'd have to ask her eventually anyways.) But keep some ground rules in mind.

  • Stay reserved. It's aggressive enough having someone ask you out, so avoid being overbearing while doing so.
  • Give her an out. Don't corner her, make sure it's easy for her to walk away if she needs to. DO NOT ask her in an elevator!!!
  • That said, do make sure it's relatively private. The two of you chatting, not a group of coworkers. You don't want to add social pressure to an uncomfortable situation, so avoid an audience. (They can be nearby, as you said it's just a big working room of desks, just avoid asking her right in front of them.)
  • Don't rush into it. Chat with her for a few minutes before asking, so you can bring it up as part of the conversation. If you just run at her and blurt it out, she might not know how to react because her mental state hasn't adjusted to you yet. This will allow her to be at ease when you ask.
  • Keep it low key. Say you like her, or you're interested. Don't confess your undying love and that you want to father her children.
  • ONLY ASK ONCE! If you ask, and she says no, then she now knows you're interested. If she later decides she's interested, she'll come to you. If you ask again and again, that's where harassment comes in.


I'd go with something along the lines of:

"Hey, so, I really like talking with you like this. And I don't know if there's anything there, but I'd kick myself if I didn't at least try to get to know you better. So would you like to go out for coffee sometime before work?"
This way it's hesitant, and hopeful, not already assuming the attraction exists or overbearing. You're clearly asking for a "date", but it's couched in the language of getting to know the person better in the first place, so it's not asking for immediate commitment or anything.

If she says no, smile and accept it. Tell her that's cool, you still like having her as a friend. Keep things friendly, and take your cue from her as to whether she's done with talking for the moment.

If you play your cards right and keep it low key, you'll still come away with a friend and no HR complaints.

HR ISSUES

So, in the unlikely event that she reports you to HR for just asking, as long as you were respectful while doing so and weren't aggressive you shouldn't have any issues. Just tell the truth, that you asked her out once, she said no, and you accepted it and moved on as coworkers.

THAT SAID, while workplace romances can be fine, workplace breakups are where it gets REALLY awkward. Know that, if you do enter into a workplace romance, a breakup can easily ruin your job for you. If it's messy, then HR may get involved. But even if it's not, it can make your daily like awkward.

That said, the fact that you're on good terms with your ex says to me that you know a bit about managing a breakup. Just something to keep in mind.