How can I deal with my insecurity?

[PrettyDecent]

Hi,

 

I've been divorced for a year and have done some dating. At the moment, though, I am involved in a frustrating situation with a woman (call her Sally) who says she wants to marry and start a family but doesn't know whether she wants that with me. Additionally, although I am open to another marriage and another child (my ex and I have a teenager), I worry about not having enough money to handle both children. I'm still unsure how this will turn out.

 

I find Sally very beautiful, smart, funny, and flirty. For a couple of months she was actively dating other men and calling me just her friend, but we gradually started hanging out more and more, sometimes even after her other dates. I felt humiliated to be doing this but felt like if I didn't maintain interest she would go with some other guy for good. By now I have fallen for her pretty hard, and we see each other a lot, but although she says she stopped her other dating, I feel like she likes the attention from men, and hasn't really said anything to make me feel hopeful except that she doesn't feel the same way about me now but is increasingly fond of me and may feel the same way one day.

 

Anyway, tonight she went out with a guy she dated several years ago. At one point on one of their dates, maybe even the first one, he took her to his pool and suggested skinny dipping. She refused but he stripped, and later sat down naked in front of her. She told me the story and said she finally told him to put on some clothes. Amusing enough, I guess.

 

Fast-forward to tonight, when she went out with the same guy. She emailed me about it and said:

 

"Awesome. Such an interesting night. He said I looked younger now than I did four years ago when we dated.

And he apologized quite seriously. It was a nice night."

 

So my first instinct is to ask her, well, is he still interested in dating you now? Does the compliment mean something more than just a compliment? Or am I just being insecure? And if I am being insecure, how can I find out why, and how I can become more secure?

 

Thanks for any help or advice. :-)

[AlexCross]

Hi,

 

I've been divorced for a year and have done some dating. At the moment, though, I am involved in a frustrating situation with a woman (call her Sally) who says she wants to marry and start a family but doesn't know whether she wants that with me. Additionally, although I am open to another marriage and another child (my ex and I have a teenager), I worry about not having enough money to handle both children. I'm still unsure how this will turn out.

 

I find Sally very beautiful, smart, funny, and flirty. For a couple of months she was actively dating other men and calling me just her friend, but we gradually started hanging out more and more, sometimes even after her other dates. I felt humiliated to be doing this but felt like if I didn't maintain interest she would go with some other guy for good. By now I have fallen for her pretty hard, and we see each other a lot, but although she says she stopped her other dating, I feel like she likes the attention from men, and hasn't really said anything to make me feel hopeful except that she doesn't feel the same way about me now but is increasingly fond of me and may feel the same way one day.

 

Anyway, tonight she went out with a guy she dated several years ago. At one point on one of their dates, maybe even the first one, he took her to his pool and suggested skinny dipping. She refused but he stripped, and later sat down naked in front of her. She told me the story and said she finally told him to put on some clothes. Amusing enough, I guess.

 

Fast-forward to tonight, when she went out with the same guy. She emailed me about it and said:

 

"Awesome. Such an interesting night. He said I looked younger now than I did four years ago when we dated.

And he apologized quite seriously. It was a nice night."

 

So my first instinct is to ask her, well, is he still interested in dating you now? Does the compliment mean something more than just a compliment? Or am I just being insecure? And if I am being insecure, how can I find out why, and how I can become more secure?

 

Thanks for any help or advice. :-)

 

You seriously need to grow a pair of balls and see the writing on the wall. You are being mind *****ed so bad it is not even funny. She is not interested in you in the least bit. She disrespects you by telling you things you do not need to know because you have been friendzoned a long time ago. Start dating other women and ignoring her. You will see how fast she will change her tune. She sounds like a game player anyway. Is that what you want ?

[PrettyDecent]

Well if you already have a teenage kid, why would you start another family at 40+ years old? Just to have a youngin' instead of a woman your own age?

 

You'll end up like most of the statistics - 50 years old with a couple of kids under 8 years old wondering why no women want to date a middle aged man with young kids. It's so cliche it isn't even funny.

 

Do yourself a favor and move on from the youngin'. She friend-zoned you a LONG time ago but she's keeping you around as "Plan B" in case the guys her own age don't want to marry her.

 

Thanks for the replies. She's not really a yougun, I'm 43, she's almost 40. But I hear you. I like her so much I'm willing to consider starting a family with her, but sadly I do agree with the friend-zone interpretation. I'm also plagued by a constitutional ability to hope beyond what is healthy, so I probably think it's one of those rare cases where a guy breaks out of the friend zone.

 

Thanks again for the advice. It sucks but I appreciate the honesty.

[AlexCross]

Thanks for the replies. She's not really a yougun, I'm 43, she's almost 40. But I hear you. I like her so much I'm willing to consider starting a family with her, but sadly I do agree with the friend-zone interpretation. I'm also plagued by a constitutional ability to hope beyond what is healthy, so I probably think it's one of those rare cases where a guy breaks out of the friend zone.

 

Thanks again for the advice. It sucks but I appreciate the honesty.

 

You need to go about this in a different way. Ditch her. Start dating women who don't talk about the guys they are dating. She is damaging your self esteem and you dont even realize it.

[Madman81]

You're completely and utterly in the friendzone. Stay there if you're happy with that, but it certainly doesn't sound like you are.

 

You need to get out and date other women. Stop contacting her. You don't have to refuse to speak to her, but stop INITIATING the communications. Just react to hers. And for god's sake, when she DOES contact you, don't be pissy. Act upbeat and cheerful, like your life is going swimmingly. If she asks you to come over and hang out, decline on the basis that you're busy. But again, be cheerful.

 

The reason you should be cheerful is that you don't need her pitying you. Nobody needs that in this kind of situation.

[mesmerized]

she doesnt find you attractive and never will. Find your balls and move on.