Middle aged women out there - I need your help

[speed racer]

Thank you sarap and SherryS

 

SherrySher, no we have not been romantic at all - even though I've known her for 4 months, we really only are still getting to know each other.

I'm no judge when it comes to how long you should give it before you introduce romance. I do and I don't get vibes from her - that's what makes it hard for me,

if I got any vibe, I'd have asked her out on a true date already -

 

I totally agree with you that there would be obvious signs where I should have no doubt -

Thats what I have been looking for - I was hoping that her texting me was a way for her to open the door, but

that's probably not it...

Thank you for saying there is no way you would ever be asking or joking about other men to a man you were into - you restored my faith in mankind on that one....

You are completely right - she is just being nice till it dissolves -

 

Thanks everyone,

I really really appreciate your comments and suggestions.

 

Speed

[LaHermes]

You are welcome, Speed.

 

If the vibe isn't there it isn't there.

And I am with Sherry. I also felt at outset that the "rich men" remark was very "off".

[tattoobunnie]

If she hasn't dated a lot before her husband, then she may totally not know how to date! I would call her up, and ask her, "hey, I've been having a really great time with you these past four months. I've always wanted to check this place out (insert someplace cool you've never been to), and take you as my date. Would you like to go?"

 

I just turned 39 (whud! whud!!) yesterday, and I think I'm middle-aged. I'm not really insulted by that term, although it's true that 30 is the new 20, and 40 is the new 30 - but either way, I really don't party hardy like I did when I was just 30 or in my twenties. But it's also because you can't retire when you use to be able to too. Either way, never say that to a woman, and if she looks tired and you don't really know her, keep that to yourself. Some people just look tired all the time.

 

That rich man comment - I dunno. Does she normally have a filter on, or is she a jokester?

[Wiseman2]

So? Her dating life is her business until it gets far enough along to introduce someone. Yes ask her out on a real date like dinner or something. Don't tiptoe around this much. "I'd like to take you to dinner this weekend when are you free"? Be direct. Make it clear it's not friends hanging out

She seemed like she didn't want her 20 yr old to know she was meeting me when we went out...

[sara-pezzini]

Not all women give off clear vibes of interest even if they are totally into you..... I am very shy and introverted and not a whole lot of dating experience and hurt very much by my ex, so i like to take it slow as well and i don't flirt or touch cause those things don't come naturally to me.

So if you like her give it another chance and make it clear its a date. I love that approach!

[Ms Darcy]

Not the way you are going about it acting like a friend. The problem isn't age or culture or rich men. The problem is she talks to you like a girlfriend because you act like one being this passive waiting for her to do all the work.

 

I totally agree. Be more assertive in your actions.

[SherrySher]

I agree with Sara, however I do think there would have been something by now...some kind of sign of interest other than friendship.

Her mentioning other men is a bad sign.

I guess all you can do is be direct and ask for a date (not a hang out, but a date) and see if you can either talk to her about actually dating or try to get a bit closer to her (arm around shoulder, or hold her hand) and see how she responds.

[sara-pezzini]

For me there wouldn't be any signs at all, you wouldn't think I'd be interested, not until I'm sure of a my feelings and b his interest....

So make some move and then you'll know for sure.

However i would never talk about any other men in whatever form if I'm into you, not a joke, nothing so i don't know about that one

[J Miracle]

I think the biggest indicator that this is simply a friendship is that you have asked her on dates, and she has rejected. However Shes fine with inviting you on outings that she's planning on probably doing anyways; cycling, movies ect. Classic friend zone behavior. She's allowing you to tag along it seems. Get out of that zone.

[Fun Boater 1]

So? Her dating life is her business until it gets far enough along to introduce someone. Yes ask her out on a real date like dinner or something. Don't tiptoe around this much. "I'd like to take you to dinner this weekend when are you free"? Be direct. Make it clear it's not friends hanging out

 

I'm with Wiseman2 on this, Speed. Again, just ask her out directly and make it clear you are asking her out on a date. You don't have to call it a date because asking a single woman out to dinner and some activity after dinner is very much construed as a "date". You are really overthinking this. And don't worry about her 20 year old either. 20 years old???? Think about it! Who cares what her 20 year old thinks. And another poster suggested this and might be right - this woman, if not having dated for a long, long period of time, might not "know how" to go about dating, or expressing her interest in you. If she's talking to you, regardless of the signals YOU are interpreting (and maybe interpretting wrongly) she has some level of interest in you. Don't show her your "friend" side. Show her your "man" side and pursue her. To quote a great movie - "Swingers": "Don't be the guy in the PG rated movie that everyone hopes makes it....Be the guy in the R rated movie who nobody really can decide how they feel about him"...or something along those lines. Be assertive. Be direct. Be clear. And when you ask her out on this date, have something very specific planned to offer her - date, time, name of restaurant,...etc..etc.... DO NOT use the "hey, want to hang out on Saturday" or something lame like that. Have a specific plan in your head to present to her. You can do this! Do not be afraid!

[abitbroken]

ou are really overthinking this. And don't worry about her 20 year old either. 20 years old???? Think about it! Who cares what her 20 year old thinks

 

actually, i can understand because he lost his dad at 12. I know that he is 20 now, but with the several people i know that lost their dad at that age through teenhood, it was very tough and sometimes they repeated a year of school, or are extra protective of mom.

 

Also, keep in mind, if he is close to his grandparents and aunts/uncles on dad's side which i hope he is, and she is still treated as family to them, which i hope she is, she could also not want the 20 year old to know so that he doesn't tell the in-laws. It may sound funny, but it almost feels like a betrayal sometimes when the widowed spouse starts to date - not so much for HER family, but for HIS for awhile.

 

At any rate, i wouldn't make the kid a factor - let her keep that she is dating from him for now if she chooses. She may feel a little funny herself dating again.

 

I agree you need to turn up the volume and initiate some contact with her - just light stuff ....she DID say that she doesn't want her kid to know she is dating so she could be considering that you are dating her.

 

I would start to invite out to datey stuff. Dinner and a play or performance. Somewhere where you have to dress up a little maybe. Skip pizza hut and find a quieter, more upscale place. Doesn't have to be super pricey or anything but there are restaurants that lend more towards dating.

[LaHermes]

Well, Speed, what is it going to be?

[speed racer]

I'm going to turn it up a little bit...

Make it obvious it is an actual date - I'm going to plan a night at a nice restaurant - maybe a winery. There is an outdoor art exhibit coming up - maybe that. Then take her to

dance with just us - If I get any good feedback, I'll do it again - If not, I'll lay low and not try to take it personally.

 

Wish me luck

Speed

[abitbroken]

Better yet === you are grownup enough to communicate about it. Ask questions. Ask her if she is open minded about marrying again someday. Ask her what she is looking for in dating (going out sometimes, looking for a relationship). When you call her up say "its a date, then". If she tells you she never sees herself marrying again or tells you she is just looking for someone to hang out with - then you can decide what you want to do. It should be about if she meets your criteria - matches your long term goals rather than just figuring out what she wants.

 

Maybe its easier for us because we met online - where we didn't previously know eachother so had nothing to lose by asking questions.

 

Also, you can also go out with other women.

[Sportster2005]

You're better off making a move and getting shot down, than sleepwalking into the friendzone.

 

Your age has nothing to do with this. Women like a man that steps up. Use the date word, flirt with her, kiss her. If she blows you off, whatever. I can tell you your passive approach isn't going to help. There's no such thing as scaring them off. They're interested or they're not.

[SherrySher]

I absolutely agree with abitbroken. You are both grown adults, there is no need for guessing games right now, or ever!. Communication is essential in any healthy relationship. Why not just talk to her and ask?

Then you will both know what page you are on.

[Sportster2005]

I absolutely agree with abitbroken. You are both grown adults, there is no need for guessing games right now, or ever!. Communication is essential in any healthy relationship. Why not just talk to her and ask?

Then you will both know what page you are on.

 

Ask what? Do you like me? Being an adult does not preclude being romantic and having some game. Really gals, you want men to just come up to you and sheepishly ask if you like them? By all means ask her out. But I never think it's a good idea to ask them how they feel. That just drains all the fun and excitement if they're interested. And if they're not interested it's going to be very awkward. It's one thing to say no to being asked on a date, quite another to say no to probing questions.

[SherrySher]

Sportster, it does not have to be childish..you seriously thought we are meaning to ask if someone likes you? Is this preschool?

Two people can sit down and have a discussion and it could be asked if the other one is wanting or is comfortable to start a relationship or if it's not something they are interested in.

I mean, these are grown ass adults..why can they not just SPEAK to one another and be open as to what is going on?

[LaHermes]

Agree Sherry Sher.

Geeze, there is a lot to be said for straight talking. Telepathy doesn't exist but the way humans sometimes carry on you'd think it did. The tone of the conversation is what is important. A light hand is required.

[Wiseman2]

Great phrase, describes it perfectly:

sleepwalking into the friendzone.

[SherrySher]

Op has been out with this lady a few times now and cannot tell if it's hang outs or is she is interested in dates.

So ask for goodness sake!! I might have a different approach if these were young teens, awkward and vulnerable are a bit more handle with care, but 40 something's? Geesh!

 

You're not going to ruin any romance (if it exists) nor will it be awkward if she says she's not interested. After all, people need to know what the heck is going on.

The way OP described everything, this really could go one way or the other...friends hanging out, or possible dates.

Just talk to one another, it seriously can't be that hard.

[speed racer]

I know communication is essential, but there needs to be some vibe of attraction -

If there isn't, why go any further -

 

The vibe was there for a few weeks - just enough life to make me think about talking to her about a further relationship.

Your right, don't need to be Telepathic, just need to have a sense to carry it further.

 

Its not there.

 

Speed

[Alsananick]

Here is a lil piece of advice. You shouldn't ask advice from women only. So you met her 4 months a go and you haven't even kissed her yet?

[LaHermes]

Correct, Speed.

 

There needs to be that vibe of attraction. And if it isn't there it isn't there.

 

Just to remark Speed re the "middle-aged" stuff, hI heard a few days ago of an acquaintance (widow) of 65 who has re-married a widower, presumably around that age too.

 

And another friend was telling me some time back how he had been at the engagement party for a couple: she 80 and he 81. Way to go!!!!

[Jibralta]

Oh yes, One more thing, this is going to sound weird, but yesterday while we were riding, she ask me where all the rich guys hang out?

I don't know if she was kidding - It was quite strange....

 

This is the most telling thing, in my opinion. Forget the "rich guy" part. It says that she's looking right past you for relationship options. If you want to date her, you have to make your intentions known or it won't have a chance of happening.