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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.
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 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)
Last edited by Jim B.; 02-11-2014 at 05:15 AM.
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