Is it over or is there a second chance?

[ZeframInventorofWarp]

So I'm a 21 year old man. Interested in my former high school teacher. She's a really beautiful and intelligent woman in her early forties. I know I pick the easy ones. I saw her recently when I went to my former school and she seemed rather happy to see me. We had a nice chat catching up but when I went to ask her for a coffee at the end I'm embarrassed to admit that I choked. Now I ****ed up I know but here's my question...is there a way to un**** it? I mean there has to be a second chance somewhere right. I've been running my head thinking "if I went back it might be creepy". I still have her email from way back when I was in her class I never weeded my contacts and thought about shooting her an email but that might be creepy too. Especially since, A: Those emails might be monitored and B: I'm really not sure what I would say at all if I even did.

 

So did I really just permanently **** this or is there a way to un**** it? I mean we had a nice time talking and I was too ****ing bitchy to actually ask. How do I get a second chance, is there one?

 

But going back, Jesus.

I just think it might be a little creepy and kinda weird 'cause look. I went there rather unintroduced and randomly to go visit and do the rounds talking to former teachers and then I just "happen" to go back a day or so later? Or even a week later?

Besides what the **** would I have to talk about at that point? Everything's really been already said that I could otherwise work with, we caught up on the last five years. After that I'm just kinda poking at squirrels here to get my foot in the door, "how was your Sunday?" Not a very good conversation topic.

Doesn't help that I am ****ing HORRIBLE at talking to women and I do mean ****ing HORRIBLE. I'd almost consider going there again in two weeks with the bull**** excuse of looking to speak for my company as a literary or entrepreneurship thing and handing her a paper of poetry about her that I write or something. Because if there's one thing I am an EXPERT at...it's words. I know it, she knows it. I ****ing aced her English class. And not just 'cause I was teacher's pet and paid EXTRA attention. This is the woman who called me "wise beyond my years". If I could just get a damn poem to her that could possibly say more to than I could ever hope to in a million years myself.

Maybe tell her how damn beautiful, sweet and intelligent I find her. How damn gorgeous she is.

But how the hell would I get it to her short of actually going back?

[MountainGirl111]

I'm not indicating that I in any way am being judgmental, but do you think perhaps the vast difference in your ages is what's really making you super nervous and got you thinking it would be "creepy"? I don't know. You wrote the word "creep" a few times in your post. It is quite an age difference. I know a few people who do it and are happy. But you're thinking it might be creepy. You've actually contradicted yourself quite a lot here. I think that's because you are so unsure of yourself.

[Garcon1986]

First question - is she open for a relationship and currently looking? You don't want to trammel onto a married woman's life, it can get literally dangerous if you end up dealing with a protective husband.

 

Next, you are a bit old to be choking on your words when asking somebody out. You could use her work email and ask her a benign question such as, mind if we communicate via personal email now that I'm graduated from your class?

 

Next, you should never have the scarcity mindset. I respect you for going for the smart women with achievements. If she knows you are this nervous, there's going to be some loss of respect here for you as dating potential.

 

It's your job as the man to create the environment where she is comfortable going out with you. There is no way to use logic to convince a woman to like you. The simplest way is to create interesting conversation with humor she likes. Then express your interest at some point when you know she is happy being around you as a person and not as a student, and ask her out to a simple date.

 

In the meantime it is not OK for a guy to be this nervous approaching girls. I would suggest you talk to as many women as you possibly can in your life, ideally through joining clubs which have activities you like so you can be natural . Try to get to know them as people and not sex pedestals - that way you have a chance of them being comfortable around you. Men are like dogs when it comes to affection, and women are like cats. There's nothing you can do to convince a cat to like you if you already did something for it to not like you. The cat's gotta be comfortable going towards you. Go towards women with the sole goal of creating conversation, then attractive conversation, then longer and longer interesting conversation without explicitly needing to bed her on the first day. That way you take the pressure off yourself, so that when your special lady comes along, you can really knock her socks off with your gentlemanliness and confidence.

[MountainGirl111]

"Bed her"?? hah! Is that how guys talks about women? I chuckle. That sounds more like barn talk. (not that there's anything wrong with barn talk) But as long as we're talking barn talk we need to git the accent right.

[MountainGirl111]

OP, seriously. Calm down now. It's not going to help you if you continue to be all worked up here. Beddin' a woman takes STRATEGY. Pure n' simple.

 

Strategy.

 

Ever played chess?

 

Think before you make the next move....think long and hard. Think about the fact that you are soooooo nervous even at the THOUGHT of getting in touch with her again.

 

I don't think that's a good sign.

 

You just need to be yourself and live your life. If someone is right for you, truly right, I'm not saying you will bump right into them, but you've GOT to be yourself, you've got to love yourself and you need to be free and comfortable in your own skin, irregardless of other people.

 

If you do decide you are indeed going to bed this woman...then again, get back to strategy.

 

What is going to bring you the most happiness?

[ZeframInventorofWarp]

I'm not indicating that I in any way am being judgmental, but do you think perhaps the vast difference in your ages is what's really making you super nervous and got you thinking it would be "creepy"? I don't know. You wrote the word "creep" a few times in your post. It is quite an age difference. I know a few people who do it and are happy. But you're thinking it might be creepy. You've actually contradicted yourself quite a lot here. I think that's because you are so unsure of yourself.

 

Well. Yeah obviously freaks the **** out of me. I'm horrible talking to women my age let alone her age.

Also, you know, I am her former student, odds are I get shot down.

[ZeframInventorofWarp]

OP, seriously. Calm down now. It's not going to help you if you continue to be all worked up here. Beddin' a woman takes STRATEGY. Pure n' simple.

 

Strategy.

 

Ever played chess?

 

Think before you make the next move....think long and hard. Think about the fact that you are soooooo nervous even at the THOUGHT of getting in touch with her again.

 

I don't think that's a good sign.

 

You just need to be yourself and live your life. If someone is right for you, truly right, I'm not saying you will bump right into them, but you've GOT to be yourself, you've got to love yourself and you need to be free and comfortable in your own skin, irregardless of other people.

 

If you do decide you are indeed going to bed this woman...then again, get back to strategy.

 

What is going to bring you the most happiness?

 

 

 

This went to bedding real quick somehow, I never even once mentioned that. Granted I'll take what I can get but I'm really interested in her romantically. I'm so ****ing nervous for 3 reasons: She's female. She's older than me. She's a former teacher.

I'd be out of my depth with just ONE of those damn things. Odds are all three? They don't equal very much success.

Also all of my ideas to fix this and get a second shot at asking her and NOT choking are pretty stupid so far.

[ZeframInventorofWarp]

First question - is she open for a relationship and currently looking? You don't want to trammel onto a married woman's life, it can get literally dangerous if you end up dealing with a protective husband.

 

Next, you are a bit old to be choking on your words when asking somebody out. You could use her work email and ask her a benign question such as, mind if we communicate via personal email now that I'm graduated from your class?

 

Next, you should never have the scarcity mindset. I respect you for going for the smart women with achievements. If she knows you are this nervous, there's going to be some loss of respect here for you as dating potential.

 

It's your job as the man to create the environment where she is comfortable going out with you. There is no way to use logic to convince a woman to like you. The simplest way is to create interesting conversation with humor she likes. Then express your interest at some point when you know she is happy being around you as a person and not as a student, and ask her out to a simple date.

 

In the meantime it is not OK for a guy to be this nervous approaching girls. I would suggest you talk to as many women as you possibly can in your life, ideally through joining clubs which have activities you like so you can be natural . Try to get to know them as people and not sex pedestals - that way you have a chance of them being comfortable around you. Men are like dogs when it comes to affection, and women are like cats. There's nothing you can do to convince a cat to like you if you already did something for it to not like you. The cat's gotta be comfortable going towards you. Go towards women with the sole goal of creating conversation, then attractive conversation, then longer and longer interesting conversation without explicitly needing to bed her on the first day. That way you take the pressure off yourself, so that when your special lady comes along, you can really knock her socks off with your gentlemanliness and confidence.

 

 

 

I'm choking on my words because I've asked 3 women out in my life over a ten-year span.

I think the last time I had a romantic encounter with a woman was about two years before Trump was elected.

 

Also, she is definitely not married. I already knew that before today but there was definitely no ring on that finger.

Granted I have no idea, she could have 3 boyfriends and a girlfriend for all I know.

Either way, I doubt sending an email is a good idea. I'm gonna wrack my head trying to figure this out.

[MountainGirl111]

Well. Yeah obviously freaks the **** out of me. I'm horrible talking to women my age let alone her age.

Also, you know, I am her former student, odds are I get shot down.

 

Dude! Something that freaks you out this much and is so intimidating to you can mean a few different things.

 

One--her age alone intimidates you...talking in sheer numbers here.

 

Two--her being your former teacher.--can you get past that? ..OKAY....NOW here is where it gets tricky too...back when you were her student and if she had sex with you THEN that would be illegal and gross, right...like Just*Not*Right...!! If you go on to have a sexual relationship with this woman as you or she or BOTH of you going to feel like it's still too awkward STILL because she still feels like your teacher and you still feel like her student. You go to kiss her but in the back of your mind.... think she is still your teacher and it shouldn't be happening.

 

Three--Do you think she would like a romantic relationship with you? What's your feel on that? Are you afraid she'll say no?

[MountainGirl111]

This went to bedding real quick somehow, I never even once mentioned that. Granted I'll take what I can get but I'm really interested in her romantically. I'm so ****ing nervous for 3 reasons: She's female. She's older than me. She's a former teacher.

I'd be out of my depth with just ONE of those damn things. Odds are all three? They don't equal very much success.

Also all of my ideas to fix this and get a second shot at asking her and NOT choking are pretty stupid so far.

 

You're stacking the odds against yourself here, bud. How do you like those odds. If I were in your shoes, I'd say it don't look good and it certainly don't feel good. No, there is a way to more peace and happiness. I think it's a good sign when it's more calm and you don't feel so nervous. I mean, some nervousness is okay....but this nervous? Hmmm. Not sure....

 

You've got to have an Ace in the hole when you feel the odds are stacked against you.

 

Play it smart. Never let anyone get the best out of you. If you feel lost, find a strategy that works.

 

If you try to kiss her and she kicks you in the shins that's a very bad sign.

[ExpatInItaly]

I think you are unlikely to get the results you want here, OP.

 

It's not a shot against you personally, but a woman in her 40s is probably not going to have much interest in her 21-year-old former student. I get that it happens occasionally, but the odds are not in your favour. I say that as a woman in my late 30s, who is also a teacher (I teach adults), who also sometimes gets approached by my own former and much younger students.

 

You could send an email and see how she responds, but I would keep your expectations low.

[BaileyB]

I think you are unlikely to get the results you want here, OP.

 

It's not a shot against you personally, but a woman in her 40s is probably not going to have much interest in her 21-year-old former student. I get that it happens occasionally, but the odds are not in your favour. I say that as a woman in my late 30s, who is also a teacher (I teach adults), who also sometimes gets approached by my own former and much younger students.

 

You could send an email and see how she responds, but I would keep your expectations low.

 

I totally agree.

[ZeframInventorofWarp]

I think you are unlikely to get the results you want here, OP.

 

It's not a shot against you personally, but a woman in her 40s is probably not going to have much interest in her 21-year-old former student. I get that it happens occasionally, but the odds are not in your favour. I say that as a woman in my late 30s, who is also a teacher (I teach adults), who also sometimes gets approached by my own former and much younger students.

 

You could send an email and see how she responds, but I would keep your expectations low.

 

 

 

I guarantee you every one of those men/boys? are at least happy they got the chance to get shot down by you. That's all I want here, the chance to at least get the no or yes, most likely overwhelming no. It'd be different if I asked and she said no, okay it's over. But I choked and thoroughly ****ed this up for myself.

I just want to find a way to make it known in a non-creepy or weird manner and be able to not keep wondering. 'Cause as long as I choke there's always still a chance, slim as it may be. And honestly, a chance is sometimes worse than a no.

[nospam99]

Disclaimers: other than pure sexual attraction (Raquel Welch perhaps? - no, she's only 14 years older and no longer of interest), I never had and can't imagine having a romantic interest in a woman 20 years older than me. Also, at 21 I did not have the confidence to 'play the card' I'm about to describe.

 

First, try to get a home or personal cell phone number. Then phone her in the evening and ...

 

Hi Ms X (or first name if you have established a first-name-basis). It was so good to see you again last week. I really enjoyed our conversation. I'd like to get together with you again some evening for coffee, drinks, or even over dinner to continue that conversation. Do you suppose I can charm you into joining me?

[kendahke]

I dare say that if she was your teacher, then she more than likely doesn't consider you as a romantic option, probably has a man already and doesn't want to date someone young enough to be her son.

 

I'd stick to women in my age range and definitely not someone who used to be my teacher.

[Larry56]

You'd be surprised how many milfs are looking for boy-toys. I say just email her you want to meet up again and see what she says.

[ExpatInItaly]

I guarantee you every one of those men/boys? are at least happy they got the chance to get shot down by you. That's all I want here, the chance to at least get the no or yes, most likely overwhelming no. It'd be different if I asked and she said no, okay it's over. But I choked and thoroughly ****ed this up for myself.

I just want to find a way to make it known in a non-creepy or weird manner and be able to not keep wondering. 'Cause as long as I choke there's always still a chance, slim as it may be. And honestly, a chance is sometimes worse than a no.

 

This is a bizarre mentality, OP.

 

You have this woman on a golden pedestal raining with angel tears. If she senses that, it will put her off as it comes across as desperate. If you insist on contacting her, OP, you are going to need to project a lot more confidence. That's why much younger guys rarely actually appeal to women around my age; they tend to lack the confidence that comes with age and experience.

 

As for "milfs" looking for "boy toys" - I can honestly say that among my peers (later 30s - early 40s) I know none who actually do this. I'm know they're out there, of course, but it's a largely overblown school-boy fantasy.

[kendahke]

You'd be surprised how many milfs are looking for boy-toys..

 

they are not the majority of women, though and they are not as great in number as you believe.