Should I just ask out my friend and see what happens or at least talk to her and see where we stand?

[reggierags]

Sorry if it's a long post but this is starting to affect me and I'm not sure how to either move forward or forget about it

I'm a guy, she's a girl, we're both 31, we work together though she is planning on leaving and it's not a serious job for either. We've known each other for a while and have been flirting a bit here and there until the past two weeks when she literally just said she broke up with her boyfriend asked me out for a drink after work

She said it was one of the best nights ever and she was happy to finally get to know the mysterious me. She found excuses to touch my hair, beard, nose many times, bump our hips together, let me feed fries in her mouth. We ended up at her apartment though nothing happened, way too drunk. She gave me a tour, took me to her bedroom then her bed though soon she was nauseous and asked me to get her an ice pack, when I came back her shirt was almost off because she was having hot flashes I guess, and was just lying face down suffering. I left after a while

She's confided in me about her mental health, including things like her therapist being surprised she broke up with her ex. Tells me about bad sex life they had and how she's just looking for more of a connection

On many days I walk her from work to her house because she's asked if I could, that's how we became friends, but this Friday she changed it to "do you wanna walk me home?" with a big smile, hard to say no to that. She also mentioned in passing that she wanted to go somewhere with me the next day but is having money problems.

There are some bad or maybe iffy things, like calling me her friend, then again that's what we were (are?). She's had a rough week with the hangover, meds chemical imbalance, a bad fever, among other things. She's thanked me for supporting her so much this week and being a great friend, even sending me a good morning text and another one where she was grateful I'm always checking in on her. But overall she barely texts and has long radio silence periods, like since yesterday. We had plans to hang at her house, not exactly a date yeah, but she said "I woke up with a really bad fever ". She didn't answer to what I wrote and I'm guessing I'll just see her tomorrow at work. Her phone says last seen since she sent me that message. The plans were he idea btw, I just re-confirmed them

I really like her but like I said not being sure where we stand is starting to affect me a lot. Neither of us wants kids, we're in the same stage in our lives, both areligious, and I love how open she is with me and makes me open. She doesn't seem to have problems getting in my personal space such as when we're all in a group she comes right next to me even if she wasn't close. While I don't do that very much on the other hand, I try but it's hard for me. Perhaps she is looking for that though. Should I just ask her out and tell her I want to take her out on a date? Or first have a conversation with her? Perhaps hold her hand or something cause I know I haven't been very physical and I would hate it if that pulls her away

She recently broke up with that guy and I broke up with someone three months ago. I know I'm good, she says she's good but hers is so more recent. I'm afraid of overstepping my bounds. Anyway, thanks for listening. Any advice is deeply appreciated.

 

[Cerwin Vega]

It's easier to apologize for "overstepping your bounds" than to kick yourself every day for not trying

 

[Dr.Suave]

TLDR. Just man up and ask her out bro.

 

[Gamisch]

We all been there at least once. I hate it to be friends with a woman I like. Period.

At some point the two of you had a equally good time with each other. And that's cool , even if you are " friends". But now it shifted; she has a lotta fun but at the same time you are frustrated. Read the forum, women simply love to have a ghey best friend. That frustrates you (unconsciously perhaps). The beast inside you wants to tear her love box apart!

You either soft next, or you go all in . At this point it's the frustration that needs to be eliminated. Either by stepping up and being ready for a rejection, or by escalating and you'll fcuck her. It's a win win situation for YOU now.

It will hurt even more when she finds a new guy and rub it in your face. And the "irony " is that you can't even blame her.

I would probably soft next and take my L. But it does sound like you can still escalate this and get some pvssy. But, mind you! After that there are many many chapters left to be written, and they might NOT be happy pages.

 

[BackInTheGame78]

Just escalate next time you are alone with her but realize you may be the rebound guy.

Less talk, more action.

 

[reggierags]

Just escalate next time you are alone with her but realize you may be the rebound guy.

Less talk, more action.

But like at work? Since she's been too ill for out past two meetups

Today she again asked me to walk her home but we just talked about random ****, she didn't even mentioned what happened to her on Saturday. If we were alone and out I'd make a move to know wtf is happening, but right now I'm clueless

 

[reggierags]

We all been there at least once. I hate it to be friends with a woman I like. Period.

At some point the two of you had a equally good time with each other. And that's cool , even if you are " friends". But now it shifted; she has a lotta fun but at the same time you are frustrated. Read the forum, women simply love to have a ghey best friend. That frustrates you (unconsciously perhaps). The beast inside you wants to tear her love box apart!

You either soft next, or you go all in . At this point it's the frustration that needs to be eliminated. Either by stepping up and being ready for a rejection, or by escalating and you'll fcuck her. It's a win win situation for YOU now.

It will hurt even more when she finds a new guy and rub it in your face. And the "irony " is that you can't even blame her.

I would probably soft next and take my L. But it does sound like you can still escalate this and get some pvssy. But, mind you! After that there are many many chapters left to be written, and they might NOT be happy pages.

Thanks for your answer! I'm not really interested in her for sex since I need a connection for that, which I felt, and she seems pretty similar in that respect to me

I am frustrated, yeah, but more about not knowing what she wants. If she wants nothing then fine, at least I know. But her avoidance and then wanting to be with me in random situations is puzzling

I'd love to escalate it, yeah, but if she keeps getting ill during our planned meetups then I just feel I can't. Not at work at least

 

[reggierags]

It's easier to apologize for "overstepping your bounds" than to kick yourself every day for not trying

In any situation though? Like I said we mostly see each other at work and after work. She asked me to walk her home today, again. At work she keeps her eyes on me when we're in a group together finds random excuses to come to my work area. Not the best situations to "overstep my bounds" I feel
I mean if she suggests we do something I'd definitely say yes and if it actually happens this time I'd do something to let her know. But either she doesn't want to or is waiting for me to just do it

 

[BackInTheGame78]

But like at work? Since she's been too ill for out past two meetups

Today she again asked me to walk her home but we just talked about random ****, she didn't even mentioned what happened to her on Saturday. If we were alone and out I'd make a move to know wtf is happening, but right now I'm clueless

And you actually believe that?

 

[reggierags]

And you actually believe that?

That's I'd make a move? Kinda..

 

[BackInTheGame78]

That's I'd make a move? Kinda..

No that she conveniently was sick on the day you were supposed to come over and have her alone one on one behind closed doors.

Not once but twice.

 

[EyeOnThePrize]

@reggierags
Why are you waiting on her to take the lead? That's drying up her panties and pigeon holing you into the position of her emotional tampon.

You don't have to grab her tits or something. One day when you're chatting, nudge the topic to something remotely sexual and joke about your own sexual prowess or tease her about her thick as$ or something. Avoid this lame meta conversation you want to have, that's such a soy move. Talk is cheap anyway. Just have fun with it, if she responds negatively then tease in a dismissive agreeable way and never bring it up again.

As far as I can tell you've been orbiting her and waiting for her to make an excuse to start jerking you off or something. She is probably getting kinda bored with you because you've become incredibly predictable. Do you ever say no to hanging out with her? Are you ever busy with something else? Why the hell not?

Let me guess, there are absolutely no other prospects in your life whatsoever. Please tell me I'm wrong and you're just a really nice dude with an enormous hammer.

 

[reggierags]

No that she conveniently was sick on the day you were supposed to come over and have her alone one on one behind closed doors.

Not once but twice.

Well to be fair she was in and out of work all week being nauseous and with headaches. She told me so and I saw it, she wasn't doing well on some days. As I mentioned she was having a chemical imbalance due to new meds. She even told me the day she out of her therapist's office to update me on what was going on. Thursday she was a mess, Friday she seemed better, then saturday she was apparently not well again. Could she have lied? Sure, but doesn't seem like it to me based on what I saw throughout the week

 

[reggierags]

@reggierags
Why are you waiting on her to take the lead? That's drying up her panties and pigeon holing you into the position of her emotional tampon.

You don't have to grab her tits or something. One day when you're chatting, nudge the topic to something remotely sexual and joke about your own sexual prowess or tease her about her thick as$ or something. Avoid this lame meta conversation you want to have, that's such a soy move. Talk is cheap anyway. Just have fun with it, if she responds negatively then tease in a dismissive agreeable way and never bring it up again.

As far as I can tell you've been orbiting her and waiting for her to make an excuse to start jerking you off or something. She is probably getting kinda bored with you because you've become incredibly predictable. Do you ever say no to hanging out with her? Are you ever busy with something else? Why the hell not?

Let me guess, there are absolutely no other prospects in your life whatsoever. Please tell me I'm wrong and you're just a really nice dude with an enormous hammer.

Well I did tell her I couldn't bring her to my sister's wedding that she invited herself too last Friday. She was excited about it and a bit bummed when I said it was too late.

I don't have any prospects right now nor do I ever, I do just let them happen most of the time. I got out of a relationship 3 months ago and she handled the "initiation" as well as most of my exes. Yeah I'm not into "excerting my sexual prowess" since I feel relationships are more than just that. If it's not in the bedroom I won't really do it

I do love your "just have fun with it" though. That is what I usually do but not knowing where she stands makes me doubt myself you know? If I can just get her out one day I would hold her hand or something, I'm just not very used to it and can't find the right moment

If she's bored why does she keep reaching out though? She basically only talks to me at work. Wouldn't just ignoring me be a better choice?

 

[EyeOnThePrize]

Yeah I'm not into "excerting my sexual prowess" since I feel relationships are more than just that.

I think you've completely misunderstood me. I said to tease and joke about it. So for example if she says she's feeling sick, you say you've got some vitamin D for her, goofy stuff like that. Relationships take a while to develop, initially it's just casual fun, don't overthink it.

That is what I usually do but not knowing where she stands makes me doubt myself you know?

You don't know where she stands because you haven't taken any risks to find out. So nut up and try some sexual jokes or something before she loses all respect and treats you like a unic (which may already be the case).

If she's bored why does she keep reaching out though? She basically only talks to me at work. Wouldn't just ignoring me be a better choice?

You're not a threat to her, you're not mysterious to her, in fact you're so docile that she can treat you however she wants and you'll probably be ok with it. When she wants some attention she'll come and fart in your general direction knowing you'll bend over and take a big sniff before thanking her and eagerly asking for more. She gives you breadcrumbs to keep you guessing, most women do this with clueless guys.

Over time she loses respect for you because it's obvious you're into her but don't have the balls to take risks and escalate. Act like a background character and you'll be treated like one.