Encounter with a Mature lady

[lobowolf]

Apologies, if the subject misled you into thinking that it will be some (fictitious) erotic story of my encounter with a mature lady. But this thread is under 'Matters of the Heart' and I assume it is in the proper section.

I need some advise. I have noticed that some of the samsters here are quite good at giving genuine advice and guidance so I would like to seek their inputs for my case too. I have no intention of starting this thread with some erotic encounter with her but I would very glad if some of you could suggest some valuable inputs.

I am a guy in my early 30's (still single) and I have been seeing a mature lady, who is in her late 40's for the past few months. Over the past few meetings she has given me some mixed signals and I not sure how to proceed.

ABOUT HER
She is a single woman (never married) and really takes care of herself and looks younger than her age. She is of mix parentage, Pakistani father and Chinese mother, so that will give you a fair idea on how she looks like. She stays alone but have two tenants staying at her house. She is very independent and know how to present herself well and I like her choice of dressing, nothing loud but very elegant. She knows how to carry a conversation and she is a nice lady to be with. Looks wise, you can pass her without a second look but you will certainly notice her.

OUR ENCOUNTER
The first time I encountered her was for 'The Platters concert'. I have an interest for the oldies songs and so I was looking for a partner to watch that together. I couldn't get my friends to go out with me, basically because they were not interested in the genre of songs and the ticket price was $100+. Finally, I decided to post in Craiglist about the concert under 'Strictly Platonic' and by evening I received an email from her, along with her contact and age. We talked over the phone and we decided to meet up just to know that we are both serious about the concert. We meet at one of the malls and I was quite surprise to see this pleasant woman.

CONCERT EVENING
On the evening of the concert, she wore a low cut blouse, which had a lacy covering but it did not hide her cleavage. After the concert, we head out for the Boat Quay for a drink and she told me that the beer will be on her, to which I agreed. It was on a Saturday evening, so we sat there and talked for hours, sitting by the riverside. That evening was very pleasant, because a storm was brewing at that time and there was this cool wind and with the display of the brilliant stroke of lightworks from the lightning. We were there till 3am or so and then went our separate ways.

SUBSEQUENT MEET UPS
We met several times in between for movies, evening walks and concerts at Esplanade and Marina Bay Sands. Despite the age gap, I really enjoy her company. Sometimes, in the evenings, we would go to the FairPrice shop to listen to the old songs. But there has been no physical contact, like holding hands and walking. She is very frank and humorous, which I like in a lady.

SOME MIX SIGNALS FROM HER
* On our first outing, while having beer, out of the blue, she asked me whether I watched pornography. I was quite taken aback but I did admit to her that I do. I am still curious why she asked me that.
* Last time she got tickets for a movie (generally, it is I, who book the tickets online), she booked the couple seats. Interestingly, when I told her that she got a couple's seat, she was apologetic to me, saying that she was not aware of it. I got confused with her intentions (if at all there were any, though it is possible that she made a blunder).
* Wore a short dress for that evening (I am mostly in fleshy ladies but her slender leg did caught my attention, which she has really maintained well), though at other times she wears skirts upto her knee.
* She mostly initiates the outings.
* While watching concert at Esplanade and Marina Bay Sands, I generally take my binoculars and she would often rub her shoulder with mine, (on the pretext) asking for it.
* Last time I met her near her house, she showed me her block where she stays.
* She recently asked me whether I am willing to watch the movie Dictator with her, considering the content of the movie (We are watching this on 20-06-2012, and I have booked a couples seat telling her that it gives a better view). She told me earlier that she will be busy this week and we can catch up for the movie next week. But when I informed her that the movie is not going to last beyond 20-06-2012, she somehow agreed to meet up.

DILEMMA
She did mention earlier that she is seeing another guy of her age, whom she met online but she added that he is married, with his family back in his home country. This gave me a fair idea that she is also on the look out but, whether for company or additional needs, is a subject for debate. I am not sure whether they are having any physical relationship, considering that they are in the same age range but the thought of it made me feel jealous. I understand that she is single and will have her needs, but not sure till what age a woman has her sexual drive/needs (though it may vary from individuals).

RECENT NEWS
Recently, I have noticed developing an attraction for her physically. If you check my FR here, most of my encounters are with mature ladies and not with SYT, so it was quite natural that I found myself attracted to her. Now, I value her friendship more than the physical part. But I am in a fix whether I should let her know about this, considering that we are both adults and should be able to handle it (??). What if she is also interested in me likewise but waiting for me to make a move? And if I don't make a move, then I might be missing out on something good. Or is she someone who knows how to play the game well??

Despite the age gap, I am willing to take the plunge but at the same time it would be a shame to end such a good relationship with her just because I made the wrong approach. I would like to play safe and want to make my move only when I have enough evidence - more of a calculated risk

How do I know/read her signals well or make my feelings for her known, in hints, without making it too blunt. What are the physical signatures or body languages that I should watch out for or observe? Is she interested in me just because of the company or is she also willing to take the dive with some young guy? Or, am I blowing things out of proportion or am I missing her whole (obvious) signal?

I would request you to kindly pen down your thoughts/advice on this. I would appreciate those to those who share your concerns. Thanks for reading through my post.

[asdfghjkl]

why not tell her directly?

[jj_jj]

she asked me whether I watched pornography
She mostly initiates the outings
she would often rub her shoulder with mine, (on the pretext) asking for it..

She wants you to F her but do you ?

I value her friendship more than the physical part
it would be a shame to end such a good relationship with her just because I made the wrong approach

[JuzNiceM]

if a RS started purely from physcial. it is FB.
if a RS started purely from fetish, it is fetish
if a RS started as friends, it might lead nowhere becoz u wouldn't wana lose it but it can also b fulfillg since u both knows wat u want n seek for.

just enjoy e outing, more n more hint will be dropped. after all she has already let down her guard. wats stressing u to proceed further?

The biggest hint is, she is still single at her age, so probably the chances of you landing her is low. there is always a better guy out there for her than you.

[Ichigo_Kurosaki]

deleted post

[Gaofar]

Good morning Singapore!

Dear TS,

Base on your info, it is rather straight forward to most people that you enjoyed the company of your GF (looking at the things that's happening I assume she is your GF as of now lah.. ).

You said that you are worried of showing the wrong kind of signals to her, not wanting to show that you are desperate, yet wanted her to know your intent. Bro, at your age and of your taste of fine arts, I'd say you ought to know that you have nothing to lose but to gain and thus should just go ahead and grab this chance.

You mention that you are jealous of her mentioning that she is seeing another married guy, but why didn't you interpret that as she is giving signal to you that she is hoping that you are the one instead? If she is not serious with you she would not be informing you of her other relations, if she is taking you for a ride and not being wanted to be serious with you..

That said, I've got to input some "exemption clause".. It does shows to me that you are not confident of yourself to show your true feelings to other party, for fear of denial and rejection. It doesn't matter if you (or us..) are reading the wrong signals at all. Honesty, as far as I know, is the best form of confession. Let her know of your feelings, but of course don't force her a "yes-no" situation, more like if she did not want a serious r/s as of now, be a gentleman and so be it. You could even end it off with something like she may says no to you now but you let her know that you are willing to wait for her, that kind of stuff.

All these you just have to be sure of your choice. Love transcends through all ages, nobody says you must marry someone who's younger than you, the other person must be "higher or shorter" than you, or such kind of silly rules. End state, if you are dead sure of your choice, let your other party knows about your decision and intent, let them know of your confidence and seriousness, with room for them to think and not feeling pressured, and if things doesn't pan out well but still able to keep in touch with each other and not be awkward about it, that my friend, will be the best scenario situation that you can hope for.

(Disclaimer: Due to the nature of your looks, your handsomeness, your way of speech, your etiquette manners, your hairstyle, your level of confidence, how you carry yourself, your height, etc., results may differ from advised.. )

[DO_YOU_BJ]

Simple la, just fuck her 1st & see how things go from there.
Worst, breakoff remain as FBs or friends lor
Both sides still win wat

[AlexV]

this is one of the better posts i have read in a long time. great story.

The conservative approach: Tell her directly that you are developing feelings for her, and hope they might be reciprocal. But, that you value your friendship and if she is not reciprocating the feelings, you are more than happy maintaining the friendship.

The best approach: after a movie, go for drinks at a pub with live music. After 3 or 4 drinks, just try to kiss her. If it is success, she'll allow it. If not, you can blame it on the alcahol.

Some realistic concerns to think about: the age difference raises issues, such as, she may not be able to have kids and you may want them? When you are 50, she will be 70.

Good luck.

[gigigagago]

Dear TS, as yours is a sincere post with a genuine intention, I strongly believe you deserve to have candid and earnest inputs in reciprocation. So here's mine:

Like some who have already suggested, I do support - and would also do so if it were me - to confess of your interest in her. IMO, she has laid bare enough of her hands to you of her status, what's going on with her and where she is in her life right now, without putting out too much to save her basic dignity. For me, she has done her part well enough. Although we'd never really know if that's the real deal, my suggestion would stand that you confess your attraction for her.

I guess the key to how you do it is the biggest thing you have to manage now. Let her indulge in, and hopefully be flattered by your honesty, but also making sure she understands that it's not something she has to make a big topsy-turvy life-changing decision on. Let her know the things you like about her, let her be reminded she has those things and you see those things in her. However, you would graciously keep your distance or take things further the way she seems fit. Offer to put the ball in her court; let her know you really want her to hear about how you feel, that's all.

I would also suggest letting the jealousy of the other man slip by first during this first confession. You don't to transfer this gravity to her now. Feel her out first. If she reciprocates, you can then consider whether you want her to know, whether she'd appreciate this jealousy as a form of affection. Play this by the ear.

I hope that helps and you would achieve the best outcome (be it any way) with this woman you like. Best of luck.

[LeGarcon]

Hello bro. Read your post and think that her signals whilst positive, shows a little holding back on her part. She might also be afraid to lose this friendship, presumably due to her being older than u and not wanting to appear to be a cougar.

What exactly are u looking for? An FB? Of course with all such delicate situations, if u initiate an FB relation, if she's not into it, you are most probably going to lose the friendship. Would you risk that? Weigh your options.

Anyway how did your movie date go?

[asdfghjkl]

if i read correctly, she is about 20 years older than you?

[Ladyrain]

Just go with the flow? You are not going to ask her, are you going to be my gf? Can I date you? Do you like me? That kind of thing?
The "oh no.. We are going to kiss.." the sudden gaze" that passionate kiss and love making.. Let it flow.

[spermswimmer]

I into COUGAR and MILF.

But don't forget they are so much clever in "playing the game" on young men.

If you know how to play their game, Then it is best to keep them as FB

[hotstuffm8]

trolololol

[DylanC]

Mature women are very sexy I guess if you feel good with then that is all that matters.