How to navigate friendship and romance?

[MrNobody1111]

Several months ago, I worked alongside a girl (let's call her Sally) at my previous job. When we first met, she was already in a relationship, but as time went on, we both left the company. Since then, she went through a tough breakup with her boyfriend, thus preventing me from asking her out at that point in time.

A few months later, she invited me to her birthday celebration. About a week later, we hung out together for the first time, just the two of us. In our conversations, dating was a frequent topic, and we would openly share our thoughts and experiences. However, despite these discussions, we've never directly addressed the possibility of dating each other. There have been occasions where she'd make jokes about us getting married some day. And she has inquired about my dating life before, even stating that I'd be a catch.

I must admit that I'm really into her, but I'm unsure about how to approach asking her out. I've never asked out someone who started as a colleague or friend before. Are there specific things I should keep in mind or avoid when doing so? Any advice on this matter would be greatly appreciated.

[Superstickyone]

Just ask her if she would like to go on a date with you.  It's as simple as that.

[Wiseman2]

56 minutes ago, MrNobody1111 said:

, she invited me to her birthday celebration. About a week later, we hung out together for the first time, just the two of us. 

She seems interested, so just ask her if she would like to do something this weekend.  You'll get a better sense of things by doing that.

[MrNobody1111]

5 minutes ago, Wiseman2 said:

just ask her if she would like to do something this weekend.  You'll get a better sense of things by doing that.

Interesting advice. But I wonder how to progress things. As of now, we're just friends. But if we do do something this weekend, I would want to make it clear that I like us to be more than that. But putting that pressure on her also seems like the wrong way to go about it.

[MrNobody1111]

11 minutes ago, Superstickyone said:

Just ask her if she would like to go on a date with you.  It's as simple as that.

Would it be more appropriate through text or in person? In person, we'd already kinda be on a date. Via text seems bad in itself though

[Wiseman2]

3 minutes ago, MrNobody1111 said:

. But putting that pressure on her also seems like the wrong way to go about it.

Invite her to something date like, not just hanging out going dutch.

There's no "pressure". Obviously you don't want to be friendzoned, but if you don't ask her out, that's where it will stay. Texting, calling, in person doesn't matter. 

[Batya33]

44 minutes ago, MrNobody1111 said:

Interesting advice. But I wonder how to progress things. As of now, we're just friends. But if we do do something this weekend, I would want to make it clear that I like us to be more than that. But putting that pressure on her also seems like the wrong way to go about it.

I've been in that situation.  Ask her out for dinner Saturday night and or buy theater tickets and then take her out for a drink.  She'll get the hint!

[NighttimeNightmare]

4 hours ago, MrNobody1111 said:

But putting that pressure on her also seems like the wrong way to go about it.

I’m exactly like this, I’ve never asked a woman out on a date, always just naturally let the friendship take off and turn into a romance if it was going to become that.   
 

but I think with certain people who don’t also operate that way, you risk losing them to someone else, they may see your lack of being direct as disinterest and end up moving on. 
 

I think there’s a balance to it, like perhaps you can let her know you’d like more, but that you also want it to happen naturally without expectations of any sort.   You can let things unfold under an umbrella of being opened about having feelings for her and wanting things to work out between you two. 
 

 

[Wiseman2]

10 hours ago, MrNobody1111 said:

. About a week later, we hung out together for the first time, just the two of us. 

Just hanging out is clearly a friendzone activity. So if you want to just stay friends, just "hang out" without really asking her on a date.

If you want to make it even more awkward and confusing for her and yourself, don't ask her out but blurt out that you want "more" than friends.   That way she gets the impression she's not worth asking out but you would be open to sex.

Asking someone out is not "pressure". However telling someone you're hanging out with as friends right now that you want "more" (sex) is pressure. And possibly  because of the insulting insinuation of FWB rather than a date, the end of the friendship. 

Please ask her on a real date. Something simple like dinner where you invite her and pay.  Have the courage to step up. 

[NighttimeNightmare]

 

6 minutes ago, Wiseman2 said:

However telling someone you're hanging out with as friends right now that you want "more" (sex) is pressure and possibly  because of the insulting insinuation of FWB rather than a date

That’s not even remotely close to what I meant