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 coffeelovinlawyer
Joined: 11/12/2013
Msg: 1
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Dating guy out of my league and scared (he is 27 I am 41)Page 1 of 3    (1, 2, 3)
Two and a half years ago, I was on business for an extended period of time. During this time, I met a man who was also temporarily out of town, and we had the most amazing whirlwind romance. At the time, our differences seemed irrelevant. We just connected so well. Regarding our differences, I was a 39 year old attorney with average, maybe slightly above average, looks, who could use to lose a couple pounds. I am moderately successful as an attorney, but by no means very well situated. He is like perfect ten gorgeous and was 25 at the time. There was just immediate fireworks. I had no time to analyze it. So, after six months we both went back to our respective homes (five hours from eachother) and tried to have a long distance relationship, but it didn't work. He ended up in relationship with a gorgeous girl his age. We kept touch.

A few months ago, both of us now single, reconnected. We have not yet seen eachother. We talk all the time on the phone and Skype and text. He wants to consider me moving there until he finishes grad school, then him moving here. I feel very in love. He gives me every indication that he's into me.

The problem? I'm terrified to see him, because I don't want to be rejected. He keeps trying to visit. I have been in the middle of litigation and working every day of the week. I have aged 2 years since we were together and gained 30 pounds. I feel like I'm aging by the day. He does nothing by reassure me that he loves me. I'm just terrified that he will take one look at me naked and be repulsed and reject me. I have lost weight since we started talking, but I'm running out of time. And not much I can do about the fact that I'm an average 41 year old woman. I'm thinking of cutting it off before I get rejected. What should I do? I especially would like insight with any men in their late 20s early 30s. Thank you!
 LiliMarleen
Joined: 5/24/2009
Msg: 2
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:12:34 PM
I think you're putting several carts before the horse if you think you're in love before you've even seen him again and talking about moving.

You have already found out that long-distance doesn't work for you, so I don't really see what you can possibly do here. Are you really going to MOVE for a guy you barely know and find a new job five hours away from home? What are you going to do with your children?

What are you going to do if things don't work out? You don't sound as if you're very confident that they will.

Why did things not work out the first time?
 coffeelovinlawyer
Joined: 11/12/2013
Msg: 3
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:16:58 PM
My kids are now grown and out of the house.

My firm will transfer me.

Not sure why they didn't work out first time. After six months together, we both moved back. We talked about moving, but I owned a home, still had kids in the house, and he was just starting grad school. We both hated long distance, and neither of us could move so we ended it.
 Whisky_River
Joined: 12/2/2015
Msg: 4
Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:18:41 PM

I especially would like insight with any men in their late 20s early 30s.

Lol....I don't think we have anyone in that age range on here anymore....
Just older gents that will pant after anything breathing.....just kidding....sorta.

I'll give my opinion....While you are waiting...though.
I say...just do it!
If he doesn't like you as you are....you haven't lost out on anything. Cele've....
The love of my life was a hottie and 10 years younger than I....lasted until his passing....about 18 years.
Through the years...I gained weight and lost...so, did he....
We were blind to the age difference and weight changes....good luck!!
 LiliMarleen
Joined: 5/24/2009
Msg: 5
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:24:17 PM
If your firm will transfer you, and your kids are out of the house, what do you have to lose. Just go for it!
 VikingHoosier
Joined: 5/8/2015
Msg: 6
Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:35:05 PM


I'm terrified to see him, because I don't want to be rejected. He keeps trying to visit. I have been in the middle of litigation and working every day of the week.


It should be good to know if there's still any type of connection. Meet once. If he does "reject" you, you'll have closure. If you cut it off to avoid possible rejection, you might have "what if?" anxiety. Shouldn't think about moving. Getting back with an ex can be short lived.

People can find time if they want. My impression of people in the legal field is there are long delays in work and stretches of "nothing" where you could find hours to spend with him.

He probably has changed in some ways in the past two years. Being with the gorgeous girl probably changed him, and he might have new life experiences / outlooks.

If he's viewed as a 10 by significant numbers of girls, he may be unavailable soon.

When I was his age, my three main girls were college age. The first time I dated someone 40+, I was 41, so I cannot relate to his situation. Age differences become less strange the older people get because the ratio gets smaller, a double edged sword because he has a larger pool of traditional age range girls.
 Chromis1
Joined: 9/9/2015
Msg: 7
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:41:24 PM
Haha, age 30 sailed by me half a lifetime ago but you don't need a young buck's opinion to know the correct answer.

I agree with Whisky and Marleen. Really, do you have any other choice? If you try, you either win or lose. Win, and life is grand. Lose and you'll nurse your wounds a bit, then life will be grand again. A rejection won't scar you for life. Indeed, it may steel your resolve ... whatever that may be.

Do nothing, then spend many years ruefully wondering "what if?"
 daynadaze
Joined: 2/11/2008
Msg: 8
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:44:09 PM
Until you start meeting again in person, I would suggest you stop living in the fantasy world and get some perspective. That fact is that you may not like each other, in person, but holding him off won't make it not happen, and stop making yourself the whole problem, what if you find he isn't really what you want. Being a perfect 10 (in your eyes) is hardly the basis for a lasting relationship, pay attention to him as a person, people are not objects. Start dating again, before you jump ahead, you are experimenting mental masturbation, put your feet back into reality. And do not give up your job, your home, your life (are your kids ready to have no place to go) if you cannot move on if moving in with him doesn't work out. And are you both able to provide equally in a relationship? Don't end up with no place to go and no way to move on.
 coffeelovinlawyer
Joined: 11/12/2013
Msg: 9
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 1:56:18 PM
I agree we need to meet up in person. I'm planning trip in two weeks.

He is well situated and has always contributed equally.

My kids usually stay with their dad when home from college. I have considered seeing them less though.

My firm will transfer me, so I have a job there.

We were both in relationships while apart, so neither of us have been on the shelf .
 coffeelovinlawyer
Joined: 11/12/2013
Msg: 10
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 2:00:58 PM
Let me also clarify that his looks have nothing to do with why I like him. We meet on an intellectual and an emotional level like I've never felt. But his looks make me insecure, because I know the nature of men is to find the youngest and most attractive woman.
 PollyR107
Joined: 4/8/2016
Msg: 11
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 2:28:32 PM
Don't feel insecure, OP. He must really like you to try to re-connect. For him, you're probably a 10 as well. Everyone has got their own type. A 10 for you may be a 6 for me:)

I'm slightly older than you and was once approached by a guy who was 13 years younger than me. He knewthe age gap from the start and it was never a problem for us. However, to make a relationship last, one needs other factors also, like what daynadaze said quite well in her post.

Getting to know him again (re-start dating) is the first step. Also have a plan b in place in case things don't work out between the two of you.

I never let fear of being rejected prevent m Enron doing anything. Life is full of surprises, you just got to try and find out. Otherwise, what-ifs will be with you for several years to come.

Best of luck
 gtomustang
Joined: 6/16/2007
Msg: 12
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 2:31:38 PM
Maybe being far away and working created stress in both of you, and that helped make the relationship work, and then you both returned to comfort zones and that's why it didn't. Sometimes sex with a hottie does blur things a little bit.
I think one of the questions to answer, if you haven't already, is what happens when he moves to where you are--will there be fallout you're playing house with someone your kids age?

If not, then everyone else is correct--stop living in fear and find out what's going to happen. If its not meant to be, then its best you rip off the bandaid now, find out, and start the healing. I know, no one wants to wake up from the dream, but it will always be nothing more than a dream, until you move forward. And don't worry about how you look naked, its not going to get any better as you age :) He might as well find out now, what if you fall in love and three years later he trades you in? I know, that's a brutal way to put it, but you're so worried about it you try to hide it. Best to test the boy out and see how he feels about it all.

Dale Carnegie wrote a long time ago about how to get over fear of failure. Imagine him actually rejecting you, and where do you go from there. Do you fall apart? wither and die? or does it hurt if you expect it (ie, not caught off guard by it), then you get over it, then you feel like at least you lived, and then you move on, and you look at the next guy you wish to date and think, hey, I got a 27 yr old, i'm hot stuff!

if you can see yourself coping with failure, imagine that you bounce back from it, then failure is less scary. You realize you can handle the fallout. its not great, but its not the end of the world. and you fear it less.
 FullMoonGuy
Joined: 3/7/2014
Msg: 13
Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 2:47:20 PM

we had the most amazing whirlwind romance.


tried to have a long distance relationship, but it didn't work.


He ended up in relationship with a gorgeous girl his age.


Yeah, there's nothing like taking up with a "gorgeous girl" while pining away for a lost "amazing" relationship.



There was just immediate fireworks. I had no time to analyze it.


I feel very in love.


What should I do?


Cross-examine.
Then deliberate.
 Ouija2025
Joined: 6/11/2014
Msg: 14
Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 3:05:49 PM
^^^ he ended it once with you for a woman his own age.
I'd not be counting on it working out this time.. but meanwhile you have to get your insecurity under control.
Mercy read like a 13 year old girl! LOL
Who knows why he looked you up gain.. I've heard they always come back
Good luck whatever you decide :)
 LetitiaLeGrande
Joined: 3/22/2015
Msg: 15
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 3:16:31 PM
He is still a young man who will grow and change a lot and you are heading for middle age. You have gained quite a lot of weight as you say and I would be sending a picture of the way you are now and let him see how you look. At least you would be spared any possible rejection in the physical. Or you could lose weight, gain more confidence and perhaps find someone more suitable when this liasion fizzles which it inevitably will. He is thinking of how it was in those heady halcyon days but in everyday life, the gloss soon fades and the rose coloured glasses fall off. .If he wants to have a family he may well look for the younger/hotter sooner or later but some men do like older women if they are not inclined towards a family.
 skier34
Joined: 5/11/2008
Msg: 16
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 3:18:17 PM
"But his looks make me insecure, because I know the nature of men is to find the youngest and most attractive woman."


...says the 41 year old woman, who went after the "perfect 10" 27 year old male.

Looks like its not just "the nature of men".
 LetitiaLeGrande
Joined: 3/22/2015
Msg: 17
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 3:57:10 PM
Please dont tell us that his looks meant nothing. There was chemistry and that does not happen without the
physical attraction. You cant tell me you didnt have sex with the guy and that is what he wanted of course and perfectly natural..
 Ladyinred0407
Joined: 2/6/2016
Msg: 18
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 4:17:24 PM
This reminds me of the conversation I had with my mom, the day after Christmas.
Me- So Mom, I'm concerned about.........
Her-Oh no I couldn't...................
Me-What if you could..................
Her-Yes but............
Me-Ok, what if you...............................
Her-Well I don't know about that......
Me- Good grief mom, you do realize this conversation has just gone full circle, right?

OP You will never know what you could have had, if you continue to find excuses, and worry over the unknown, and agonize over "what ifs".

Buy a new dress and high heels and go for it!
 Whisky_River
Joined: 12/2/2015
Msg: 19
Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 4:23:25 PM
^^^^^^Yep....Lady after my own heart!
If the mutual attraction is there.....don't miss the opportunity.
No one knows how long any relationship will last...even if he was your own age.
If he thinks your hot and treats you well....give it a go.
You're a lawyer...so, just don't be stupid with any of your assets.
Have fun!!
 coffeelovinlawyer
Joined: 11/12/2013
Msg: 20
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 4:27:39 PM
To respond to a few comments:

He did not leave me for another woman..that came 9 months after we decided not to date.

Also, I have pictures of myself all over Facebook..
Like all kinds of current pictures..he knows what I look like and calls me sexy every day. We also start almost every day sending a picture to eachother once we get in office.
 SS4544Spd
Joined: 8/31/2016
Msg: 21
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 4:29:29 PM
I'm well past the age range you desire comments from....but I was 27 once. I'd say "go for it," but I wouldn't put my life in upheaval mode for it. I would try to do something on a trial basis (no pun intended)...what that is, who knows...but I definitely wouldn't sell the house or anything like that, unless that's what you want to do anyways. And that's nothing against you, because you are an attractive woman....(curious if the pics are after the +30 pounds?...I know the fine ladies here won't like THAT question...)...either way, you can lose the weight .....but if he's still a "gorgeous 10," be careful...but you seem to know the score 'bout that. Easier said than done, but I'd go into it looking for a good time together and no other expectations other than that. And see where it goes. A 27 year old guy, especially a "gorgeous 10" likely has more oats to sew...unless he's an anomaly. If he's in the legal industry, maybe that would help bridge the gap that the age difference would suggest.

Good luck.
 coffeelovinlawyer
Joined: 11/12/2013
Msg: 22
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 4:31:31 PM
Pictures are after weight gain.
 SS4544Spd
Joined: 8/31/2016
Msg: 23
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/3/2017 4:33:37 PM
Whisky:

Just older gents that will pant after anything breathing.....just kidding....sorta.


Hmmmm...is that payback for the "hourglass figure" controversy?
 hearton64
Joined: 6/9/2016
Msg: 24
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/4/2017 2:25:35 AM
If anything ruins this, it will be your insecurities.

Or if at some time in the future, he wants kids.

Moving 5 hours for someone and uprooting your
life with no guarentees sounds like a bad idea.

Until you stop seeing him as "out of your league"
no good can come from this.
 gtomustang
Joined: 6/16/2007
Msg: 25
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Dating guy out of my league and scared (he is 27 I am 41)
Posted: 1/4/2017 9:46:26 AM
"I've heard they always come back"

>>>for the same reason junkies look up the old dealers who gave 'em a break. When we want pleasure, we return to those who gave it to us, just in case lightning strikes twice. Can't hurt to ask. But others move on. The OP may just rekindle this romance, and find out he hasn't "gotten better with age".
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