Gentlemen, I need some advice and tips here regarding older women. I know there are dating sites and other sorts of online discussions boards that are probably more suited for "relationship" types of questions, but heck I've been here long enough to come to know that despite all the car talk and grease-monkey jibber-jabber, many of you know a thing or two about the finer things about dating and women. Maybe there's something to be said about those who drive fine old Mercedes as having a refined knowledge of women, particularily older ones. Besides, a number of you here are well-expererince in life, so anyway without further ado....

Okay, so I have in the past posted about a mad work crush...I would say maybe three years ago was when I first made a random post about it because I had to tell someone. This was no ordinary work crush--it was a stupid, silly, and oh so hopeless crush on my "boss." I mean it was someone at the top! I know, stupid, but love (if love it was) is stupid. I put boss in quotation because she wasn't my immediate boss but rather the second in command and was my boss's boss and essentially the boss of everyone in the organization, which was a government one. For the three or four years that I was aware that I had a huge crush on her, I remained mature and professional and respected her and her title enough to keep this crush to myself. I didn't do or say anything that would get HR involved because I wasn't stupid However, over the years I sort of made an effort to put myself in front of her by communicating with her more, usually via e-mail about random stuff that we might have talked about in person. Of course, I also tried to impress her with my work, and she would give me praises. Nothing over the top. We really got a good rapport going. I so badly wanted to let her know how madly in luuurve I was with her but couldn't.

The opportunity came when the director announced her retirement via e-mail about a year ago. Wait--what? Retirement? How old is this lady, you're probably wondering. I think she is going on 55. Of course I was bummed but then I decided that I had better do something. I gave her a card wishing her well and stating that I'd like to keep in touch. I might have said that through e-mail. She agreed. And let's say that by then she would have to be utterly clueless if she didn't know I liked her...a lot!

So fast forward. We have gotten together two times already for lunch and dinner last year. We're probably getting together this Thursday for dinner. Now the "dates" are really spread out, so it's not like we've been getting together often. This upcoming date will be our third time to get together since her retirement. I've been pleasantly surprised that our dates were not filled with awkward silence. On our last date we stayed pretty long talking. I'm in my late 30s, and despite the age difference and not to mention social and economic differences, we really got along well and had much to talk about. I still can't believe we had gone out together. Who knew! But the thing is I don't know if she is being nice and friendly or likes me. Heck, I don't even have her number yet and really don't know how to get that without really knowing how she feels about me. They say older women know what they want and don't play games. If she has any sort of romantic feelings for me, do you think she would let me know? I feel like with this third date, I have to be more aggressive. The romantic in me wants to kiss her to see how she responds, or at least tell her how I feel. Would a woman her age even go out with a younger guy if she didn't really like him? I know deep down maybe it'll never work because of age difference and different life experience between the two of us, but I wouldn't mind having a relationship with her with both of us understanding that we can have a thing going even if it's just for now.

More questions later, but that's enough for tonight. Btw, reasons I like her is that she has a beautiful personality, sweet voice, sophisticated, and have I mentioned that she's HOT? She looks sort of like the Danish PM

The only thing holding her back that I can discern is the age difference. 30s to late 50s? Too much IMO.

I have had the hottest, most exciting and gratifying love affairs that I can remember, all with older women - but not that much older as in your case. Still, you should keep on tryin'.

Keep us posted. Oh, yeah, cool story, Bro.....

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'06 E320 CDI
'17 Corvette Stingray Vert

Well frosty what have you got to loose?

If you don't stick your neck out then you'll never know. I reckon there's a good chance she's waiting for ya big boy.

Third date already eh? Shift it up a gear - if you miss the gear - clutch back in - deep breath - try again; if you keep on going in 1st gear it'll run out of steam and die...

__________________
1992 W201 190E 1.8 171,000 km - Daily driver
1981 W123 300D ~ 100,000 miles / 160,000 km - project car stripped to the bone
1965 Land Rover Series 2a Station Wagon CIS recovery therapy!
1961 Volvo PV544 Bare metal rat rod-ish thing

I'm here to chat about cars and to help others - I'm not here "to always be right" like an internet warrior



Don't leave that there - I'll take it to bits!

It sounds more like late 30s to mid 50s - so say 15 years? Not bad in my opinion depending on the compatibility of the individuals.

__________________
1992 W201 190E 1.8 171,000 km - Daily driver
1981 W123 300D ~ 100,000 miles / 160,000 km - project car stripped to the bone
1965 Land Rover Series 2a Station Wagon CIS recovery therapy!
1961 Volvo PV544 Bare metal rat rod-ish thing

I'm here to chat about cars and to help others - I'm not here "to always be right" like an internet warrior



Don't leave that there - I'll take it to bits!

This may or may not be relevant but I went out with an older woman for a while. The first time I tried to kiss her, she stopped me and asked if I was aware of her age so it was obviously on her mind.

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-Evan


Benz Fleet:
1968 UNIMOG 404.114
1998 E300
2008 E63


Non-Benz Fleet:
1992 Aerostar
1993 MR2
2000 F250

I think that you have laid the groundwork respectfully and perfectly here, and from my perspective personally, you may have likely found one of these.

There is no longer really opprobrium attached to these situations, and I am sure that this lady is very grateful that you did NOT create an awkward situation by approaching her romantically in any way that could be misconstrued by the HR Department, which in Governments, has little enough to do that they will jump all over stuff like that if they sensed an opening.

I know that because I too, took early retirement from the Government around 55, like she has chosen to do.

I remember your story (hazily, at this point) when you told it here before, but not the details, honestly.

You've established the groundwork, she knows you and likes you, so I think you are NOT at all too young to approach the gal; You can reminisce about persons and situations at work when she was there, but you should on this, the third date, get her to talk about everyone's favorite subject - themselves.

It should become crystal clear, as she talks, what her personal dating situation is.

I've done the online dating thing for awhile, and I am 65 years old now, so she would be in the lower levels of acceptable dating range for me, and I know for a fact, that there is a HUGE pool out there of available single females of her age, probably over HALF of every female in the USA 55 or over is unattached AND available for dating.

Show genuine interest about her. Ask about her interests, and her FAMILY; ask how she fills up her days now that she doesn't have to work; ask whether she enjoys life, and whether retirement is what she imagined it would be, making the choice to pull the plug earlier than most folks do; in other words, draw her out, and show real interest in HER.

That will draw out the information you need, but make her more comfortable around you, and view you as a friend, and feel more comfortable and relaxed.

I'd avoid ALL mention at this point, any mention of anything crude, joking or otherwise, of a sexual nature overtly. Women this old have been around long enough to be VERY familiar with those kind of approaches, and I've been told time and again, by them, stories that would amaze and shock you about what men have said to them - and such encounters make them feel like they had just taken a bath in a sewer. But that you probably know.

I'd suspect there is a fairly decent chance you have a pretty good chance for a romantic encounter, here, as women that age have VERY lusty sexual appetites, still, that will absolutely amaze you if you get a good one. And remember also, Frosty, that statistics indicate that the people of EITHER gender that are single at that age, over 50% of them have had NO sexual relations for over a year's time.

Let me say that again: Over a YEAR! That means there is a very good chance she is more than ready -- for YOU!

If you look at the Vodka martini thread, you can see my last girlfriend, who I cut loose right before Christmas, reluctantly but of necessity, I felt after a relationship that lasted near a year. I think all else aside, and so did she, our sexual chemistry was sizzling, the best for both of us, we ever had in our lives. She took me to the moon! Over and over.

She is 63 years old!!!

So yes the hotties ARE out there, and they don't advertise overtly.

VERY good chance you have found one. Judging from your timeline, I think there is a good chance here she likes you and could be MORE than ready.

If it happens though, understand it could easily morph and grow into a relationship, at least in her mind though. Early on, if things go well, you will have that talk - about the ground rules, expectations, and the future. Probably you know that, but I'm just saying. You owe it to one another, as good people.


I wish you well.

edit:

Oh yes, one more thing. On your next meeting with her, bring her some flowers, or even a small book of verse, maybe something like Maria Ranier Rilke, or Khalil Gibran, (for example), had written. That counts as a nice gift and ALL women like that. It is so romantic and they LOVE to be courted. Almost ALWAYS. In fact, I hear that they keep "score".

And the point system is: one point for every gift! Doesn't matter WHAT the gift is, it is the thought. It's the gift, the act of giving, the THOUGHT of them PERSONALLY, that matters and makes them feel special...and makes them feel YOU are special, too....

A new car, a house, a bouquet of fresh flowers, a gourmet truffle in a gift box - ALL equal ONE point.

And they LOVE confidence in a man. I have read and heard that over and over. Enough to believe ALL women adore that trait.

At the end of the 3rd date if it went well, end it with a full-on hug. If it lingers then go for the kiss. lolz

__________________
1991 560 SEC AMG, 199k <---- 300 hp 10:1 ECE euro HV ...

1995 E 420, 170k "The Red Plum" (sold)

2015 BMW 535i xdrive awd Stage 1 DINAN, 6k, <----364 hp

1967 Mercury Cougar, 49k

2013 Jaguar XF, 20k <----340 hp Supercharged, All Wheel Drive (sold)

go for it.

My grandfather, with one kid heading to college, and another a junior in high school, married a 25 year old woman when he was about 47. They were happily married for nearly 40 years after (until his death).

The age difference is less relevant depending on the personalities involved, but I agree with kartek, its probably going to be on her mind, so id find a way to blatantly address it and put it to rest. Plus the fact that you were technically subordinate to her at work as well, not just a random guy, but a guy who used to work for her.

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This post brought to you by Carl's Jr.

What is the question? You are already there so might as well run with it and see where it goes. Let her know what your intentions are and if she is interested, it goes. If she decides she doesn't want to, don't waste your time. Since she is no longer your boss, the rule "He who hesitates, masturbates." applies.

__________________
01 Ford Excursion Powerstroke
99 E300 Turbodiesel
91 Vette with 383 motor
05 Polaris Sportsman 800 EFI
06 Polaris Sportsman 500 EFI
03 SeaDoo GTX SC Red
03 SeaDoo GTX SC Yellow
04 Tailgator 21 ft Toy Hauler
11 Harley Davidson 883 SuperLow

She will not let you know. YOU must make the first move.




^This. Se emboldened statements.


See above before doing this. Build the foundation first.

If it was a How-to, it'd be blank!

__________________

1980 300TD-China Blue/Blue MBTex-2nd Owner, 107K (Alt Blau) OBK #15
'06 Chevy Tahoe Z71 (for the wife & 4 kids, current mule) '03 Honda Odyssey (son #1's ride, reluctantly) '99 GMC Suburban (255K+ miles, semi-retired mule) 21' SeaRay Seville (summer escape pod)

Most of us guys, same thing.

__________________
1991 560 SEC AMG, 199k <---- 300 hp 10:1 ECE euro HV ...

1995 E 420, 170k "The Red Plum" (sold)

2015 BMW 535i xdrive awd Stage 1 DINAN, 6k, <----364 hp

1967 Mercury Cougar, 49k

2013 Jaguar XF, 20k <----340 hp Supercharged, All Wheel Drive (sold)

Not necessarily. There are a lot of self help books that helps the author not you. Look at all the psychology books out there.

__________________
01 Ford Excursion Powerstroke
99 E300 Turbodiesel
91 Vette with 383 motor
05 Polaris Sportsman 800 EFI
06 Polaris Sportsman 500 EFI
03 SeaDoo GTX SC Red
03 SeaDoo GTX SC Yellow
04 Tailgator 21 ft Toy Hauler
11 Harley Davidson 883 SuperLow

__________________

1980 300TD-China Blue/Blue MBTex-2nd Owner, 107K (Alt Blau) OBK #15
'06 Chevy Tahoe Z71 (for the wife & 4 kids, current mule) '03 Honda Odyssey (son #1's ride, reluctantly) '99 GMC Suburban (255K+ miles, semi-retired mule) 21' SeaRay Seville (summer escape pod)

In Praise of Older Women:


They don't yell.

They don't tell.

They don't swell.....

...and they're grateful as Hell.

__________________
62 220sb
67 250S
72 280SE 4.5
74 280C
77 300D
82 240D
85 190E 2.3
86 300E RIP 12/28/09
85 300SD
92 300D 2.5
00 E320 Current
Over 1,000,000 miles in Benzes, Since66

....and a whole passel of BMW 2002 and Tii

That's exactly what I was wondering.

Some do's and don'ts

Play with her, don't try to play her. Make it easy for her.

Do touch her in a light and easy, non-pushy and non-threatening way, for example, take her hand in yours. If she doesn't want you touching her then you are just a friend. (translation: not getting laid)

Look her in the eye and tell her how being with her makes you feel and tell her that you could spend a lot more time with her. Tell her you want to be more than just friends. Tell her that you have a crush on her and want to get to know her better.

Even if you already know, ask her if she is married or engaged or anything like that. Ask her what she is doing for the rest of your life.

If you feel like a fool later, that's good too. Justify it by telling yourself that she needed an ego boost.

If you regret what you didn't do then you are just a big pussy. Everyone does things that they wish they could take back later, part of living. Join the living, get busy and do something but be nice.