My natural reaction would be to walk. Never been desperate enough to play games with respect to personal relationships. I'll walk and make way for someone more desperate.

Don't know about being a pussy but I'd rather find out sooner than later that this is going nowhere fast.

__________________
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

I'm surprised no one has mentioned being the beneficiary of her retirement benefits.

__________________
1977 300d 70k--sold 08
1985 300TD 185k+
1984 307d 126k--sold 8/03
1985 409d 65k--sold 06
1984 300SD 315k--daughter's car
1979 300SD 122k--sold 2/11
1999 Fuso FG Expedition Camper
1993 GMC Sierra 6.5 TD 4x4
1982 Bluebird Wanderlodge CAT 3208--Sold 2/13

There are easier and more socially acceptable ways to marry for money ... not all rich girls are super attractive.

Oh, but they are. Money makes a 4 out of 10 up to a 9 depending on how desperate you are.

__________________
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

God I hope I am not being crude. A kiss or the attempt to have one usually leads somewhere. Rejection is always a possibility but still part of life.

From what you have mentioned you may just have to tell her you are romantically interested in her. At that point she will define her interest if any. Beating around the bush too much may indicate too much indecision on your part.

Sometimes we overthink things as well. It is impossible to establish the level of chemistry between the two of you on the site. At her age she should be able to talk about anything. Can we be more than friends is a nice soft approach as well.

With my humourous approach to many things in life I would have a ball in a situation like that. I have absolutely no ideal if you will or will not get to rattle her bones.

Rejection is a possibility. However it is better than being strung along.

__________________
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

About ten years ago I was on an outing with an old English gent and we got lost in rural England in his car, hungry tired and exhausted we chanced a pub in this unlikely, deserted area.....

They were open and served us food and drink.

Its name made us whoop with glee! (and we're both pretty much all British by ancestry)

"Old Rattlebones".

That was so quintessentially British, we thought!

\http://www.therattlebone.co.uk/





The Rattlebone is a beautiful 17th century village pub with roaring fires in the Winter, lots of nooks and crannies, wobbly tables, chairs and settles; and character oozing out of every crack in the walls. We even have a ghost, the 11th century Saxon warrior John Rattlebone!

Set in the picturesque village of Sherston, it is 10 minutes away from the historic towns of Malmesbury and Tetbury, close to Badminton, the Beaufort Polo Club and Westonbirt Arboretum, and is a gateway to the world famous Cotswolds.

__________________
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)

Wow, thanks for the replies, guys! I found all of them constructive and positive in their own ways. I'll need some time to take it all in and give a meaningful reply back. Just had a long day and my mind was a bit preoccupied with my new mountain bike fork that arrived today. Seems to be leaking a bit of oil and trying to find out the seriousness of it. The fork is air but the component that controls compression and lockout uses oil...but anyway, I was just as excited about reading the comments to my post. For some reason I can't help feeling a bit nervous about this upcoming dinner because now I feel like I've put pressure on myself to do something and make things happen.

Jim B. mentioned bringing a gift. I've never thought about doing that with her. I gave her a good-bye gift, but nothing that suggested romance Maybe I should. I better get to brainstorming because I only have a couple of days before we meet up. Flowers are out of the question, though I'd love to give them to her. They’re too...I dunno...suggestive. I like the idea of bringing a gift, but I don't know why I'm hesitant about doing it.

Regarding her status, she is not married, and I don't think she has ever married. I had thought about asking her if she's ever been married before on our last "date," but I wasn't sure if it was an appropriate question and so didn't bring it up. Would I be out of line for asking such a question? From what I can tell, she was single when we worked together and I'm sure she is still single now. In our conversations and e-mail correspondence, there's never been any mention of a man. All her friends seem to be female whenever a friend is mentioned. And yes, I’ve had my ears perked and my alpha male instincts kicked in whenever she mentioned a friend she visited or stayed with during a trip to the nether parts of California, wondering if it’s a male friend that may hint to me that she might have someone else in mind. No guy friends mentioned yet

I know her position at the org was very demanding, so I don't think it allowed her to have much of a social life. I think that's one reason she decided to retire early because she wanted to do and explore other things while she's still at the peak of her life. I don't think she has any kids only because she's never mentioned kids before, but then again I've never asked because I just don’t feel comfortable asking those questions primarily because I don't know how one goes about asking them without sounding too prying.

She and I are similar in many ways. For one she is a very private and reserve person, as am I. I bet many people from work don't know much about her personal life. She just doesn’t give much detail about her life to others from what I gather…and yet here she is going out with me, the very act itself is sharing a little bit about herself with me. Maybe I’m just reading too much into it.

It may seem all the signs are there for me to make my move, but I feel like this is new territory considering her age and life experience. A part of me is sort of waiting and wanting her to do something because, after all, she is (generally speaking) the proverbial older woman who knows what she wants. But what if she is old-fashioned and prefers that the guy make the first move? And what does this “make the first move” even mean anyway? Ah, it’s all back to high school! And speaking of which, one thing I find attractive about her is her sense of class and sophistication and yet there is this girlish charm about her. I like to think that maybe she has that butterfly feeling around me as I have when I’m around her.

I’ll get back to talk about some things people have mentioned, as it’s getting late and I my mind is fuzzy:

Age – that has never been an issue with me.

Money – retirement benefits? Hehe, nah… I don’t care for her money, and she’s not materialistic even though she made some serious bank.

Physical contact – she’s always offered a hug when we met and parted. I’m not much for initiating hugs, but maybe I should.

And aklims “he who hesitates…[well, you get the idea]”

Nobody has quantified it yet nor do we know he will get it yet

__________________
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

Don't be intimidated by her wealth, stature, and sophistication. from what you have now disclosed, it's a pretty safe bet she is available for dating. And actually it may be possible that with her retirement she has given you a window of opportunity to act.

i'd suspect also, that for all her redoubtable career experience and classy and sophisticated façade, at heart she is just like any other woman that in her heart would love a romantic relationship. And she may have an amazing dearth of experience in this area, especially with a nice guy.

But you will *have* to take the lead here - and do so with confidence, yet with kindness, humor, and gentleness, and above all sincerity.

It may take time, as her feelings of trust and safety build, but if things go well, you ought to up the ante. Another hug at the end, maybe at least squeeze her hand gently, (and if she squeezes back, you have it made!) or at least brush her cheek lightly with your fingers, as you smile and look into her eyes; when you are saying good bye/hugging or I think your lightly touching her jaw for a moment right where it ends below her ear is a very tender gesture, in my experience no woman recoils from that -- it is in its way innocent yet erotic also.

One thing important, by now you should have some idea of her interests, so BE SURE to end things by "closing the deal" by asking for a next date, at or near the end of THIS one.

You MUST do this - propose a SPECIFIC event, time and place, and then - ASK!
To seal the deal you have to ask for her phone number, for sure this time!

...Of course she might say no, give you the "friendship lecture" (all guys know what that is!) or say she has other plans ....at which time you can, you MUST, ask nicely if another time and place would work) and right then you'll know whether she is interested or it's time to cut your losses and move on or "just be friends".

This makes it easy for her.

Suggestions for a date could be so easy - a walk around the lake after a nice breakfast in a nice cafe, a visit to a new art exhibit at a museum, a trip to the zoo or an arboretum, a visit to a weekend flea market or an antique store, a bicycle dealer, or a nursery, you have tickets to a new play or a rep movie she might enjoy, ask her to go with you to help pick out a nice shirt or a sweater you could use, take a bicycle ride together, or a visit to the SPCA to check out puppies (don't buy one though!), or anything you think you guys would enjoy. When you talk to her, DO mention her name now and then; everyone loves to hear their own name!

Don't mention or hint around about sexual or physical stuff, it would be better instead to get and hold her attention on mutual interests and a shared event. Thar's an immediate need! The other will come naturally, I think, with this kind of gal.

And if she says YES! you are on the way..

BUT one more thing: You HAVE her phone number, so after a decent interval when you think she got home, DO_phone her up, and say you called to be sure she got home safe, and mention in passing the next date. (Keep it brief).

I'd say that is a MUST, (took me years to learn this) but it shows you are concerned about her welfare, AND looking forward to the next meetup.

I'd suggest one in a week, maybe two at the latest.

From what you said the time and stars are well aligned at this juncture. You've laid the groundwork over a period of years, and shown appropriate respect in all areas.

Time to move ahead! Don't overthink it though, Frosty. Be confident, friendly and relaxed.

Good luck.

__________________
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)

He's not asking gigolo level questions, give him time, a little time.

On the question of age, if you are not taking really good care of yourself you might be a little old for her.

Lick her nipples. In short order there will be either a green light or a red, and you will not have any trouble understanding which it is - even if color blind.

^^ I nominate this for post of the month ^^

__________________
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)

And progress to "South of the border, down.....".

__________________
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

Test me !!

http://img2-2.timeinc.net/people/i/2014/news/140224/olga-graf-600.jpg