A
male
age
30-35,
anonymous
writes:I'm in my early 20s, not perfect but I met a woman who's 30 recently and we really hit it off.However shes has a LOT of bad things in her past. I'm not misogynist and I have obviously slept with girlfriends but she did a load of crazy stuff when she was my age or younger. Her parents were rich but really liberal so she did stuff like **** a guy in the middle of a crowd at a gig when she was 16, or drugs at boarding school though she was never an addict. And she was a FWB with her flatmate at uni which apparently got awkward. She also got a tattoo at 14 as a dare though I know her dad and he is classy. Obviously she's older now but still a bit of "party girl" though she has a good job as do I.I have told her all the things from my past too, but I find it hard to think about hers. She is really hot, and has a good career and a degree so I'm surprised she isn't taken :lol: is that a red flag? Also I'm not really worried about this but she has a lot of male friends around her age she flirts with too.
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drugs, flatmate, flirt, her past, tattoo Reply to this Question
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male
reader, Serpico  +, writes (23 September 2016):
You have retroactive jealousy - a normal byproduct of human evolution. The downside is it will likely not get better, and perhaps will get worse the more you emotionally and financially invest in her.My advice to you - do not date her. If you want to sleep with her fine. She is obviously ok with it given her past, so no harm there, but do not engage in a long term relationship with her.One more thing to consider - save any other issue, the odds that you two work out long term given your age differences is minimal. She is 30, say you are 22. In ten years, she will be 40, you will be 32. Her looks will be fading, and her sexual history will not be. You at 32, if you keep yourself in shape and pursue a good career, would easily be able to land a woman in her early 20s - almost a full two decades less than the woman in question, and perhaps without all of the other baggage.
A
female
reader, chigirl  +, writes (21 September 2016):
 If she has openly shared/bragged about this to you, then I dont think she takes you seriously, and is just looking to use you for sex. Dont committ.
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A
female
reader, aunt honesty  +, writes (20 September 2016):
 It does not sound like you both are a good fit at all, she sounds like she is a bit wild. You need to take some time and consider if getting together with her is really what you want, her being hot is not a good enough reason, do you see a future with her? Can you look by her past? If not then end things and look for someone who is more suited to you and your needs.
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A
female
reader, Honeypie +, writes (20 September 2016):
 If her past is something you can't look past and accept, you need to let her go.
EVERYONE has a past, maybe not as colorful as hers, but we have one.
Her past has made her into the woman you see in front of you today. Maybe due to her upbringing she had more of a rebellious spirit than you (and me). No two people are the same.
Either you can accept her for who she is.... or you can't. It's not like SHE (your you) can change the past.
So really.... shit or get off the pot. (crude I know but that is where you are at).
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A
reader, anonymous, writes (20 September 2016): It's more important who she is now. Considering we all have a past and there is no way to change it. You're telling us about behavior over a decade ago; and she has moved on to become a successful and strong woman. If you ask me, I think she would be better-off with a more mature and stronger male-type. Capable of seeing her for who she is, not who she was. People make mistakes and they get second chances to redeem their transgressions. They makeup for the past by changing to more productive citizens, being good to people, and contributing something positive to society.
There are things to consider here. She sounds like a spoiled and rebellious rich girl who took advantage of her privilege and freedom. She got a lot out of her system, and much of it may have been due to family issues and boredom. Wealthy people have their problems too. Her wild behavior is sometimes typical of her class. The older generation is stuffy and conservative; while the younger generation has all the fun. They eventually come to their senses. Some don't, and things may end tragically. It didn't for her.
If you're so judgemental, why are you even wasting your time considering her in the first place? Go find yourself a virgin, living a sheltered life. That may be easier for you to handle. You're far too inexperienced for such an outgoing and assertive female.
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A
female
reader, llifton +, writes (20 September 2016):
 First off, being "liberal" doesn't mean you fuck dudes in crowds. Just throwing that out there. There is no correlation between the two.
Who cares if she has a past?? Don't we all? What matters is the type of girl she is now. Is she honest? Trustworthy? Someone you connect with? To me, that's what matters. Just because she did that then doesn't mean she would do it now.
It certainly wouldn't be a deal breaker for me. But only you know the answer to that, as only you can decide what is unacceptable for you. Good luck.
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A
female
reader, Anonymous 123  +, writes (20 September 2016):
 If you're feeling this way then I doubt you'll ever grow out of it. My point though is, why is she telling you all this? Having sex in a public place, FWB, drugs.... Why is she even taking about all this now? Are you actively seeking out this information? If you are then don't you think it's utterly pointless to dwell on the past and not focus on the present? On the other hand, if she's voluntarily disclosing all this, then she's an attention seeker and is showing off
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A
male
reader, anonymous, writes (20 September 2016): I can't advice you one way or other but when I was around your age I had a similar experience with an older woman.You will fall in her love and you will have a great time with her and learn a thing or two from her but eventually she will dump you and you will be extremely hurt from which you will come out but you will never forget her. So it is your choice. Good luck.
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A
male
reader, anonymous, writes (20 September 2016): PC answer: You're judgmental, insecure, you have control issues.
Realistic answer: You are using common sense. You are troubled by her history of troubling behavior. You find her unattractive behavior to be unattractive.
If the past shouldn't matter then why does it matter in all other areas of life except sexual history? Try applying for a job or a school or a bank loan and saying "my past shouldn't matter! What's wrong with you!?!" to all their questions.
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A
female
reader, janniepeg  +, writes (19 September 2016):
 Having sex at 16 in front of a crowd and taking drugs can not be considered fun. It's attention seeking when there's not enough love at home. At lot of wealthy families look perfect on the outside but inside there's no connection and people are emotionally empty. Her acting out could be an attempt to get accepted, to get noticed when she felt like a nobody at home. Now she is still flirting with male friends, which means her need for attention is insatiable and that spells trouble in a relationship. This is not retroactive jealousy but seeing something that troubles you if you go ahead with dating her. Just tell her you prefer younger girls. No need to tell her what you can't handle.
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A
female
reader, singinbluebird +, writes (19 September 2016):
 I think your concern shows you who YOU are and not a reflection of who she is. To be completely honest, she sounds completely comfortable with who she is. She has absolutely no concern about what other people think of her. But your concerns shows that you struggle with accepting her because most likely youre more conservative and traditional and I think you really should focus on why you feel this way. Maybe a more subtle quiet girl would be a better fit for you. YOu may be intrigued by her, but by her character I dont think shes concern about what you want or by her past.I think the real struggle here is youre not a good fit and I think you know it. Some people make poor choices or do things that may seem risky or bad, but often times our place is not to judge them but to see that their life is incompatible with ours and we move on. I dont think this girl isnt the right fit for you and your gut is telling you so.Move on and find a girl closer to your age who may be a better fit. Good luck =)
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A
female
reader, anonymous, writes (19 September 2016): I think you are being pretty judgemental. Are you interested in this woman now or just what she did years ago? A tattoo at 14? Who cares about that?! She's 30 not 13 of course she will have had other sexual partners. If the party girl stuff bothers you go for someone who isnt into that,but don't judge someone on stuff from years ago. I'm sure you've done some things when younger and more stupid that you wouldn't do now.
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A
male
reader, Garbo +, writes (19 September 2016):
 There will be people who will admonish you for having this "retroactive jealousy" and shift the burden of fault on you for being incapable of accepting her past. Frankly, though, person's past matters or why else would employers ask for a resume of it. So why should sexuality be any different? It isn't, and the problem you find yourself in is not of your making. It's her past, and just like a bad resume, if you are unable to accept it then feel free not to. Decide quickly whether you want to be with her, hot as she is, in exchange for having to deal with your internal turmoil. It would be, however, utterly irresponsible of you to string her along just because she is hot all the while you are aiming to dump her. Bottom line: decide fast what you want with her then stick with that decision.
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