Younger Man Fallen for Older Woman

If she’s going to stick around you longer than you previously thought, you better state your intentions with her soon. You meant to do it in a couple weeks anyways so hold yourself to that deadline

The problem is my contract ends in 7 months. That is around the time she will move to the new school. I don't want the awkward office envrionment if I get rejected.

Its tough cause I like her but for all intents and purposes, unless another two meetings go SPECTACULAR, i think my chances are low. But acceptance or rejection how should I

>Show my interest
>Not mentally implode if rejected
>Advance if in 1/100000 she agrees

>Be forward and state interest clearly
>Can't help you with rejection. Is it your first gf? You will suffer for months. Maybe therapy will help
>If she agrees then you can advance whatever way you like

Bit of a prompt but i got no exoerience and not mad social. Dun me through the first part about being direct and clear step by step. HOW to.

Yes it would be but im more focused on how to manage sharing the same office if no.

"I really like spending time with you. Do you want to meet more often?"
You are making the intentions pretty clear + a possible rejection won't make things awkward.

That is nice. Thanks man. But regardless if positive or negative response, how do I manage the office space we share?

No, the real problem is you’re too afraid of rejection to ever try. But I know you won’t change. You’ll keep making these threads and ignoring advice and waste the next 7 months this woman, never doing anything about it. It’s a fucked up mindset because it’s like you already know you’ll get rejected but you don’t want to get it over with and find out for real. And what if there was a chance you could’ve been with her? Every single day you wait is wasting your life.

In her case, she didn’t worried that much, she uses IUD, if the situation changed she would’ve told me, we did discussed about that, and told me she wasn’t looking to have kids anytime soon but asked me if I would have any problems with a change of mind to which I wasn’t, I did liked her very much, sadly enough she had to move and the relationship died, sad, but understandable.

In case of of positive response you have nothing to worry about.
In case of negative, it will sting for 3-4 weeks then you will get used to the feeling.

What is wrong with women? Why wouldn't a 36yo want kids? What does a human want at that age? To travel more and suck even more dicks?

I get your logic user. I do. Why not get it over with and move on? Either I had a shot or none.

But to explain my view is.

1. I have never hit it off with someone like this in a long time. I love her company. I would be devastated to lose her company if things went south. So yes you are partially right. Never mind the fall out to sharing an office.

2. I know the perfect time is not going to happen. But we still do not know one another too well. I feel a bit, just a bit of waiting to develop better understanding of one another would be better.

3. I am getting conflicting advice. Some saying take the dive or "ride the wave", both for different reasons. I have never ever thought id get positive attention from such a woman in my life. So between being new and having no clue what to do on top of, yes, fear of rejection, I am list the best approach considering the circumstances of a woman who is both in a very different part of her life than me and my own personal set of quirks.

>What is wrong with women?
well, dude people want different things and being a soccer mom isn’t in her plans, or just being a random wife making meals for her significant other
Why wouldn't a 36yo want kids?
Well she positioned her job first, she has traveled around the world, she’s a legal representative in a big ass company, she had very few relationships, (I know this due to her mom congratulating me for being with her for so long, or she rarely has time for any relationship at all).
>What does a human want at that age?
Not having a boring life... monotony is a slow killer my friend, I have nothing bad to say about her, if I can in the future, I will look for her, we still have a fantastic relation

If I'm following this then things have progressed since last time you posted? You were saying that you guys had hung out a bunch but that she was basically putting you off arranging the next time you were going to see each other. So you've moved past that?

A lawyer? It looks like her job is varied and fulfilling then?
But even so, she doesn't account for her self in 10 years. Job will become repetitive after a while. She will be returning to an empty home at 7pm waiting for the time to pass until the next day

Yes essentially. No apartment visits but going out for lunch during work hours.

Well it was, the time I lived and worked with her was where I learned most of what I know in my job, we also dabbled in real state, since that what my family does I helped with stuff in that area, trust me, letting money work for you instead of you working for money is what she, we, aim to. Some condos here and there, rent over here, Airbnbs over there, anyways I liked my time wi5h her.
>She will be returning to an empty home at 7pm waiting for the time to pass until the next day.
Meh, why stay in one place when you can be anywhere you want

Some people have hobbies they don't want to give up in favor of childcare, others don't want a family for personal reasons, etc.
People like things you don't like.

Then you should really stop freaking out every time she can't see you on the instant. This girl has given you a full month's worth of proof that she's interested in being around you and every time she has something else to do you lose your shit. That's so fucking unhealthy.

It’s just sad seeing you refuse to do anything out of fear. I hope you get your head out of your ass before it’s too late.

Well the reason I am reluctant in this immediate context besides rejection us because she is training to be a manager. She is under intensive schedule, so she technically is not under good circumstances to approach.

I know man. I know. Not an excuse but explanation is that im inexperienced and she really is something else. Hell im on here, should give you a profile of what im like roughly.

>she technically is not under good circumstances to approach
goddamnit user you will give any excuse to stay in your comfort zone. usually it’s the girl who tells the guy she’s too busy to date, not the guy telling himself that

But that is exactly what I am thinking. She is busy so she WILL say that. She even said yesterday she is too busy to hang out after school.

Manager? School? Are you attending university together? Are you teachers?

Oh boy. Everyone gets busy. But if a girl tells you she’s too busy to hang out, and doesn’t offer another time, she’s avoiding you. If she likes you, she makes time.

Not black and white. She may like him atm but not that much to make time on a tight schedule.

I disagree. If she really does like him she will make time. It might take a few weeks for her to do so, but she will.

School. Esl. She is training to be head of a school which will be opening in a few months.

Well that is more reassuring than your first but she is VERY busy. She told me what she has and she isnt lying. Cause our office is small and open enough to know.

>Hell im on here, should give you a profile of what im like roughly.

Half of this board are normies, sorry to tell you.

At the end of the day this girl is never going to ask you out, in all probability. She's your superior which makes it pretty inappropriate to date you. You will have to be the driving force. Either you've got the stones to try or you don't, and if you don't then you need to move on. This girl is no more special than any of the girls that any other guy has fallen for. That's just how you feel when you like someone. They always seem super special and a cut above.

Otherwise all you're going to continue to do is tie yourself in knots because she has to do her grocery shopping when you wanted to see a movie and it's going to give you a fucking ulcer.

Shit or get off the pot.

I have composed myself better than i have had before so no ulcers.

Here is the full context. She has 7 classes over a period of two weeks, as well as 2 weeks on boarding and a trip to shanghai for a managerial training.

She is locked out for about a month. During this period she is going to be busy.

Do i shit now ir after?

>Do i shit now ir after?
Not the same user but we both know that no matter what anyone says you’ll choose to keep waiting, even after the busy month is over

Tell her you've got a date, see if she gets annoyed. That'll tell you everything you need to know.

Quite frankly user the main factors contributing to my waiting to begin with, besides as stated above are

>I lose the relationship
>Akwardness in office
>She has just moved here to start a new life so for it to be launched into jeapordy over some under employee...looks bad for me
>others have said to wait due to the above /she is busy, out of a long relationship or she is out of my league
>Her response could be to shut me out completely

Id rather not play games but i can try to work around that.

Yes we know your life is so hard. Rejection would be the absolute worst thing to ever happen to anyone.

We do share the same office and I feel id be a wreck after. But no obviously not but I like her, a lot. And ive never been this close to a woman before. Pretty sad in hindsight but I love her friendship with me so much.

Thanks for the advice regardless anons and for your patience. I know I am indecisive and fearful but thanks.

Well I just received some pretty distressing update.

Being as discreet as I am, the whole office supposedly knows I like her and so does she. She has also been playfully teased over us hanging out. For all intents and purposes I am at best "cramping her style" or at worst making her life harder in the office by embarassing her.

I am pretty gutted but I have concluded it be best at this point I just keep my distance. I feel very sad though but it provided a lot of context for me.

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That's all happening because you are a pussy afraid to state your intentions. You should have talked to her from the start instead of dragging it like this and involving others

I kind of did considering I treated her to meals, we went out for dinner. Stating my intentions right now? Think its fucked. The interest was shown mind from my end. On top of that, the other context I may have failed to mention was that, as my manager and having moved here for a new start, confessing to her at the start was likely not going to change much. She also was likely aware the issues of dating a lower ranking colleague.

Except maybe before I took a home trip back but that boat is gone. Sadly.

Also for clarity, they supposedly knew I liked her from the very first time she came into the office and I started talking to her.

>Being as discreet as I am
lol I sure hope this is sarcasm. I’m not surprised at all that your bad case of oneitis was an open secret.
>For all intents and purposes I am at best "cramping her style" or at worst making her life harder in the office by embarassing her
You don’t know that though. You’re just speculating. I’ve been following this story since one of your first threads and it’s what you’ve been doing this whole time. You refuse to communicate your feelings and keep assuming how she feels.

Actually I got the info from one if my colleagues. Not her mind, that is true. But some have teased her over our "little dates". She laughs it off though. The former, yes that was indeed sarcasm.

So what’s next? You’re really just going to give up now?

Yes and no. She also, in hindsight also was hinting to keep things lowkey but being dense I did not cop it until my colleague spilled the beans. I mentioned it to her about hanging out IN the office and broadcast she woukd be occupied for several weeks and had no time.

So i think in the office I will back off and give her space. But I may communicate if she wants to meet outside the office and see. We are sharing two days off together this week and was going to text "quick coffee?" and see response from there.

Sounds good user. And I know you won’t take this advice, but now that you know she knows you’re sweet on her, you should use this as an opportunity to tell her about your feelings. Not in like a big anime confession way, but talk to her adult to adult and tell her you like her and want to purse something with her when her workload calms down.

Honestly user I will. I know im dragging it and pussyfoiting but I will. Its just TIMING. First it was going to be after the house warming, but that is now in limbo.

Then it was going to be after a month JUST as she was leaving our school so no complications. Now that date is all over the damn shop.

So now I don't know. But the other factor is, I have talked extensively with others outside. The long and short of it is, and my main contention us this logic which two of my main face to face sources of advice have said

>She has arrived from a new country to start fresh after a very long term relationship ended. She has come here to be a manager of a school. The last thing she wants or needs is a relationship and a low rank colleague swooning over her and making things weird in the office.

Followed by

>You enjoy her company but confessing or clarifying your feelings could throw it all away. You enjoy her company ya? Why risk it all?

Followed by

>She is out of your league and showing interest considering the above will result likely in a no. So play it cool and long

Those are the three pilkars of advice ive based my overall tempkate on and fell into because it seems the least selfish and also takes into account her situation.

But i do think and feel but failed to explain is there is a middle ground but being totally inexperienced in these situations i dont know how without potentially losing her AND making office life weird.

The young people are saying gain closure, the older not. I want clarity yes, but not at the cost of embarassing her cause desu i am immature in these areas.

Hope that explains why i am so pacey.

>Talk to her adult to adult to puesue something when her workload calms down

And now I am back at square 1. If you have time, lay out, step by step, word for word how.

I am 29 but don't know how to say this cause I want to avoid awkwardness. Its a fairly huge learning curve for me. I am playing catchup. Id love to do this smoothly but dunno how at all.

Plus it us hard that she has brushed off attempts to meet outside school so do i blubber first opportunity or try to establish meets outside?

As an outside observer, all this "logic" is silly, especially the part about
>it seems the least selfish
Making a move on a girl is inherently selfish, and you shouldn't feel afraid to shake things up. All your advice amounts to is hiding and doing nothing. How is that a logical way to get women?
I'm not trying to write a script for you but the next time you meet her for something casual like coffee or lunch, bring it up during the conversation. Don't tell her beforehand that you need to talk to her, just meet her like normal. It will be unavoidably awkward no matter how smooth you are. The hardest part is getting the conversation started. I'd probably bring up the topic by saying something like
>hey this is really awkward but I feel we need to talk about it. i heard that apparently everyone at the office thinks I have a crush on you
And from there admit that it's true, and tell her you know she's really busy but when things calm down, if she's willing, you want to take her out. Keep it short and matter of fact, don't vomit out your feelings, don't bring up her being your boss or anything else.

Thanks for that. Its selfish due to her coming here for a new life and me jumping on her while she is already busy and after a long break up.

As for your suggestion, I like it. That is the clear cut thing i needed sabs "this is really awkward", not sure what to flip on that.

>Its selfish due to her coming here for a new life and me jumping on her while she is already busy and after a long break up
Goddamn quit with the excuses. Think positive. A new life means a new boyfriend. You think if she reciprocated your feelings she would go "oh sorry user but I'm trying to have a busy new life after a breakup so even though I love you, we can't be together"? Bullshit.
Anyways good luck talking to her. Practice what you want to say if you have to, just remember to keep it short and to the point.

Alright. My last part is and honestly the huge stick in the ass is

>She puts me down

How do I manage the office environment?

And if she shuts me out. Cause I cannot emphasize how much I like hanging out with her. I feel so comfy around her and enjoy her so much.

You act like your office is going to become openly hostile if she rejects you. The worst that will happen is you'll be awkward around each other a bit, but just be professional and do your job. And if she doesn't want to hang with you anymore, then tough shit. You're a big boy, you'll survive.

Well she has invited me to her place. Out of the blue. Game, meal and movie. What to do now? This is fucking me up

Invited you over just now you mean?

I've been enjoying your threads in the same way it's oddly fun to do something really frustrating.

She knows you're into her now, though a woman her age probably always knew, they're just THAT good at picking up signals. Yes you were a naive idiot for accidentally getting your office involved but that's because of your inexperience and there is no way around that except to get experience.

For now, until she says otherwise, she's happy to hang out with you and be friends. The fact that she laughs off jokes about your "little dates" and then still wants to hang out with you means at the very least that she's not embarrassed by your companionship or the fact that people might read something into it.

Go over to her house and have fun, stop beating her (and others) over the head with your feelings for her in the meantime. When you've finally had enough of putting off the inevitable, then you can decide whether you try your luck or put the crush to rest.

Yes just at the end of day

>user!
>Huh?!
>TETRIS TOMORROW?!
>Wh-wh (no exageration) ok! You sure?
>Are you scared?!
>Hell no!
>Cool we can play, order food
>Uh...will I bring that body switch movie too?
>Sure

Literally COMPLETELY UNREADABLE. First i think she is avoiding me. Then i think i hear she wants to keep away from me. Then she gives me a gift. Then coffee. Now this. Bro im out of my fucking league.

But yes will do and thanks for your neutral advice.

It would be pretty kino (and cute) if your crush browsed Jow Forums desu

Literally impossible. Would be something out of some anime or something. No way. Unless she drops something tomorrow, impossible.

Let this be a lesson to you. After all your talk of how she’s so busy now and it will be impossible to see her for weeks, she miraculously found the time. Like says, if she likes you, as a friend or otherwise, she will make time.

This is in one way even more confounding. I thought I had a read on the situation. Ive been simulating probabilities over this by the dozens upon dozens of potential event trees. This doesn't make any sense! My head is so bloody lost now.

Thanks again for all your help. I will keep things updated.

don't forget your condoms, lad.

I wont be having sex with her man, just another apartment visit but thanks. Granted i wont be buying any or im fucked if she sees them thinking i intend sex.

No offense but you never had a read on the situation

None taken. I thought I had some semblence but obviously barely any.

For clarity, should I stay over in her place like I used to under the assumption she doesnt request me to leave anyway or just leave and give her space?

ask her if you're gonna need condoms or not.
that was a pro-tip from my aussie mate.

Trust me i wont

How's it going user, you guys fuck yet?

No man. I am visiting her today. I am on asia time. And I doubt we will its just a nice get together like we did before I assume.

Keep us posted, I am now invested in your story and I want to know if it goes well, even if there's no funny business involved.

Will do. Will post back once the night is over.