A
male
age
36-40,
*ookieOnLove
writes:I'm currently becoming very close and developing feelings for a lady older and more experienced than me. She is 32, me 26, I am a virgin, she has had 2 long relationships, I have never had one, she is the first girl i have ever had deep feelings for.I do often ask her questions about her past to get to know her better, and she answers openly, I ask why things never worked out, what was right and wrong, satisfaction, etc etc.She often says I am different to her ex's, but not really explained why, which makes me feel a bit nervous. Would it be okay for me to ask her how the other two gave her the proposition of wanting to be her boyfriend? Is that asking too much?If you were a lady, would this ring alarm bells?
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female
reader, myname1  +, writes (2 March 2011):
I am 39 my fiance is 29... I think if you want to know then ask...what harm is in that.. after all the past tells a lot about what your future could hold for you. If you do intend on being with this lady.you have a right to know so ask subtle questions at first..If she has an issue with it...then there is hurt feelings maybe that she needs to clear up. you don't need the extra baggage of her past taken out on you in the long run ... you know? take it slow and enjoy the ride..
A
male
reader, Capri2  +, writes (16 February 2011):
You can end up obsessing about her past later, and you will regret all the things you asked. You have not experience, so knowing much about her past can make you jealous easily.
Of course, that can not happen to you at all. But, is it worth trying?
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A
male
reader, CaringGuy +, writes (16 February 2011):
I myself am dating an older woman. When we first met and got to know each other, she said to me that she'd answer anything except anything to do with her past. I agreed to that. We've been happy for 2 years, and I don't care about her past at all.
There's no problem with asking questions about who she is. That's how you get to know the person you're falling for.
But I would leave her past behind. You're her future, so all you really need to know is how you can make her happy.
And clearly ask her to go out with you - she does seem interested.
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A
female
reader, chigirl  +, writes (16 February 2011):
 Yes it's a bad idea to dig into her past. That said she's mature enough to be able to say no or to not answers questions she doesn't want to. Asking basic questions related to how someone could catch her attention, or what it was about her ex's that caught her attention could be ok. But, she might not want to talk about the exes.
Typically people dislike talking about their ex. They rather want to forget the ex ever happened. It depends on what type of relationship she has with the ex. Are they still friends and talk? Or does she stay clear of them like they were the plague? If she shows discomfort about talking about them you should respect that and not ask more questions.
Also, just because you are curious and inexperienced you do not have a right to pry into her past. Her past is her own personal experience and you do not have a right to demand to know everything. If she feels uncomfortable you need to respect that. However if she is fine talking about it I don't see how your questions could become a problem.
Just keep the questions to a minimum. The best thing would be to have a talk with her about it, ask all your questions, and get it over with once and for all and not ask again.
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A
male
reader, dirtball +, writes (16 February 2011):
 Digging into her past is a bad idea. It can cause you issues that are difficult to get rid of. Sometimes it's one piece that sets things over the edge, and there's no going back.
You should not be concerned about how others asked her out. That doesn't matter. If you like her, then just ask her out. Tell her in your own way. It may be goofy and awkward, but that will also make it endearing. She knows you don't have experience, so don't try to pretend to be someone you aren't.
She would not answer your questions if she wasn't interested. I think it's time to ask her a question that matters, like will she go out with you. ;-)
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