Friend date?

So, bare with me as this is my first time actually fully venting about this, so, fair warning, I may be a little scattered. It's a little vague to keep anonymity.

I have this friend, let's call her Cat (Jesus christ, do you know how hard it is to come up with a fake name that somehow doesn't have a connection to your life personally? my roommate's cat just walked by so I settled.)
- I Digress

[ BACK STORY/HISTORY. TLDR; old friends that drifted apart and reconnected after both having failed relationships, skip if you'd like]

Cat and I have been friends for a longish time. It started out with me having feelings at first, then us just being friends for a while and then we sorta went our separate ways, she got a boyfriend and got married, and then I ended up in a LTR and well, fast forward a few years to more modern times. Cat had a kid with her dude and got a divorce, and my relationship happened to end basically the same day. And well, here we are again, full circle.

[PRESENT DAY]

I met her son for the first time recently and he's the most adorable toddler ever and we actually got along pretty well to the point where he asked where I was the next day lol. We see each other a few times a week give or take. We have this weird flirtatious kind of interaction, we have a lot in common, common life goals, common history, we're basically the same person with weird quirks, preferences, etc. She's recently been more open with dating guys and as I have been more open with dating people as well. She tells me about all of these terrible dates she's been going on and if I'm being honest, it makes me sad to see her so mistreated. Like I feel like she deserves so much more than what she's getting and what she's experiencing.
She's somewhat aware of how I feel, but I don't want to fully tell her, with the fear of screwing things up. I tell her that she deserves more than what she's been dealing with, and I've mentioned taking her out, and when we talk about it, I can tell she's holding back. Almost like she wants to say yes, but she's holding off on something.

All of this to say that I want to take her out. I'm a very outgoing, romantic, gentlemen that was raised oldschool, like I just want to show her that not all guys are the same, that she doesn't have to deal with stale ass dates, she doesn't have to deal with guys consistently trying to get into her pants, or with guys just showing little to no effort. I want to show her that there's guys out there that'll treat her the way she deserves to be treated. Sure, there's a little bit of romantic side of things, but if it doesn't go that way, I feel like I might be okay with it. you know?

I just wanna take her out, dress up, buy her a dozen roses, pick her up at her house, knock on her door, open the door for her, take her to a nice dinner with a nice view, go out to the nearby big city and do something nice, take her home, walk her to the door and don't try to get it in unless a move is made by her..

IDK, What should I do? How should I go about this? or should I just chalk this up as a loss?

Sorry this post is so long by the way. Thanks in Advance

Submitted May 28, 2019 at 01:34AM

So, bare with me as this is my first time actually fully venting about this, so, fair warning, I may be a little scattered. It's a little vague to keep anonymity.I have this friend, let's call her Cat (Jesus christ, do you know how hard it is to come up with a fake name that somehow doesn't have a connection to your life personally? my roommate's cat just walked by so I settled.)- I Digress[ BACK STORY/HISTORY. TLDR; old friends that drifted apart and reconnected after both having failed relationships, skip if you'd like]Cat and I have been friends for a longish time. It started out with me having feelings at first, then us just being friends for a while and then we sorta went our separate ways, she got a boyfriend and got married, and then I ended up in a LTR and well, fast forward a few years to more modern times. Cat had a kid with her dude and got a divorce, and my relationship happened to end basically the same day. And well, here we are again, full circle.[PRESENT DAY]I met her son for the first time recently and he's the most adorable toddler ever and we actually got along pretty well to the point where he asked where I was the next day lol. We see each other a few times a week give or take. We have this weird flirtatious kind of interaction, we have a lot in common, common life goals, common history, we're basically the same person with weird quirks, preferences, etc. She's recently been more open with dating guys and as I have been more open with dating people as well. She tells me about all of these terrible dates she's been going on and if I'm being honest, it makes me sad to see her so mistreated. Like I feel like she deserves so much more than what she's getting and what she's experiencing.She's somewhat aware of how I feel, but I don't want to fully tell her, with the fear of screwing things up. I tell her that she deserves more than what she's been dealing with, and I've mentioned taking her out, and when we talk about it, I can tell she's holding back. Almost like she wants to say yes, but she's holding off on something.All of this to say that I want to take her out. I'm a very outgoing, romantic, gentlemen that was raised oldschool, like I just want to show her that not all guys are the same, that she doesn't have to deal with stale ass dates, she doesn't have to deal with guys consistently trying to get into her pants, or with guys just showing little to no effort. I want to show her that there's guys out there that'll treat her the way she deserves to be treated. Sure, there's a little bit of romantic side of things, but if it doesn't go that way, I feel like I might be okay with it. you know?I just wanna take her out, dress up, buy her a dozen roses, pick her up at her house, knock on her door, open the door for her, take her to a nice dinner with a nice view, go out to the nearby big city and do something nice, take her home, walk her to the door and don't try to get it in unless a move is made by her..IDK, What should I do? How should I go about this? or should I just chalk this up as a loss?Sorry this post is so long by the way. Thanks in Advance