How to ask someone you see regularly out on a date, without making it awkward?

Question

Here's the situation:

There's this girl, let's call her Jane, that I've known for slightly over a year. We met pretty randomly when we were both looking for a dance partner for ballroom dancing, and the past year we pretty much only met at lessons and events related to the lessons.
During the previous year she had a relationship.

However at the start of the current year her boyfriend broke up with her, and at that point I realised that I like Jane, and wouldn't mind seeing if we could date.

Since then we see each other slightly more often, as she asked me if I would like to try out for the exercise that she does, and I ended up enjoying it (although whether that is purely because I enjoy the activity, or because she is also there, I am not sure of).

Whether or not there are any signals that she is interested in me, I would not feel confident saying. There have been some things that make me go "Hmmmmmm", but I do not have a good track record at reading signs, and know of myself that I tend to interpret things more favourably in such circumstances

The problem, and question, I run into is:

What is a good way that I can approach asking her if she wants to date, without making it incredibly awkward?

What I really want to avoid is making it that she no longer feels comfortable going to dance lessons with me, or that's she feels awkward about me asking her out.
Additionally I do not want to give the impression that I was waiting for her to break up with her boyfriend, so that I could ask her out.

Another point is when it would be good time to approach this subject with her.

I also want to make it is clear as possible that I do not mind it if she rejects me, but I also don't want to end up with a really vague answer like "Well, maybe later", as that would offer me no closure so to speak.

I hope I worded the question clear enough! It's my first time asking a question here, so anything I can do to improve the question, please do tell

Answer 1

One approach would be to let her know you'd like to get to know her better and ask if she'd be willing to do things with you outside the context of the dance related activities you both take part in. If she is interested in you then she'll likely say yes and you can ask her what she'd like to do. There's a chance she may even ask you if you mean a date - which would be great because you can simply ask her if she would like that (give her the power).

I'd say that you're off to a good start though - she has sought you out for additional activities within the scope of dancing and no one wants to dance with someone they don't like!

Take things slowly if she doesn't raise the matter of dating - these things tend to happen naturally over time if they're going to happen. Perhaps if after a few months you’ve started seeing each other several times a week and you’re arranging an activity (even if it’s just coffee) ask her if she would like to make it a date. Hopefully she will :)

Answer 2

Chances are good that she likes you, too.

Usually, women signal interest more subtly by causing them and their interest in question to spend time together, even if by no means romantically. And since she invited you to her exercise, it sounds a lot like she wants to spend time with you.
Of course, I am an outsider and can't say for sure, but I wanted to add that for reassurance.

You stated two distinct goals:
Approaching her without creating an awkward scenario and not being too direct/bashful as to cause her to go to defense and making excuses/delaying. (I find my description of the latter lacking, but you'll see what I mean.)

---

The setup

She has made clear through her actions that she likes spending time with you. Sou you should use that. In your case, as you do not want to risk your friendship and dance partnership, you might not want to be too direct.
Invite her to things friends do together. When you go out with your friends, maybe invite her, too. (Ask your friends about that, first, though.) Friends can do a lot to make someone look more attractive as group scenarios and dynamics do show your social skills as well as friends would usually try to make you look good or fun to be with, too.

Another thing you could do is invite her to dinner. I would recommend a restaurant and not your place, but that depends on cultural context and personalities (and your cooking skills). It is rather obvious in terms of where you are going with that, but it is not nearly as direct as "I want to be with you" or something of that sort.
Stating it like this would give her the option of rejecting a dinner invitation instead of you. So even her rejection would be indirect.
For this it might be best to not give a timeframe at all or a vague one. Otherwise you could barely tell a rejection from an actual excuse.

There is also the alternative of getting dinner tonight spontaneously. Maybe after dance class you ask her:

Hey, I wanted to grab dinner at [not-too-fancy-restaurant of your choice], want to join me?

It would not give her the opportunity to clearly signal "I like you, but I am not interested in dating you." (if that was the case), but you could test the waters in regards of how much she seems to be interested in spending time alone with you, in a very roughly date-like scenario.

The conversations

You did not want to be direct, so you should try to bond on the basis of friendship. This approach might not give you a direct answer of "yes" or "no" within a single conversation or even day, but it is a lot less likely to make it awkward for you to still spend time together.

Have fun together, enjoy activities together if she enjoys all that with you, chances are good you could make it work. If you have trouble looking for positive signals of "I'm into you", consider looking for negative ones of "I'm not comfortable with this". This does not mean you should try things you think could make her uncomfortable, but to see her reactions on subtle stuff. Like simple, random body contact. If you accidentally touched her hand, does she pull hers back intentionally or is she just surprised. None of these things are very clear signals, but you'll get an overall feeling with this.

If you get the right feeling, either change the subject to relationships to find out if she's seeing someone at the moment, or ask her out to something quite obviously date-like. Especially with the latter you will get a rather clear yes or no. Phrase it as an invitation and not a "I want to be with you". That way it is more likely she is going to be honest, if she intends to reject you, but avoiding being direct about dating gives her more space and opportunity to be honest instead of cautious.

---

Side note:

I also want to make it is clear as possible that I do not mind it if she rejects me [...]
[emphasis mine]

Phrasing is very important. You should certainly not have her see it as "you do not mind if she rejects you", because if that was the case how could she be interested in you if you cared that little?
What you should signal is that you could bear rejection, not that you don't mind.

Answer 3

Before asking if she wants to date you, maybe first figure out if she’s open to the idea of dating and if she’s already seeing someone.

For example, you could ask her for a coffee after one of your regular activities together. Make it like a casual catch-up instead of a date. During the coffee, ask her if she’s dating and what she is looking for. If she is available and interested in you, she’s very likely to share that with you and ask you the same questions. And based on her answer and the interaction, you could get a better sense of her interest level and whether there is a good fit between you two. With this new information, it’d be easier for you to decide if you’d like to make the next move and what kind of date would be more appropriate for you to ask her on.

Answer 4

If you've liked her for a while there's a decent chance she's already picked up on some hints that that could be the case and has decided to leave the ball in your court. This was the case for me in a past relationship where I developed a bit of a crush on a girl I was working with. I thought I had been subtle in hiding my crush but when I finally decided to admit I liked her and wanted to ask her out she didn't seem at all surprised. In the end our friendship wasn't affected and we did get out to a date after some time.

Of course we can't always expect this to be the case but I think in general it's hard to entirely hide it when you like someone and there's always a chance they've noticed little hints to start to suspect it, if they haven't changed their behavior towards you as your crush has grown they probably don't hate the idea of having your interests at least.