Dating an older woman...my insecurities about her past

[NorthernSoul]

Hi guys,

I'm 28, recently divorced and dating a 35 year old. In part due to my recent divorce where my wife cheated and left, I'm sure I'm filled with a certain amount of insecurities that I'm dealing with.

With some help from SoSuave and some confidence, I've been able to hook up with this attractive, experienced woman I work with. This particular relationship started as we were friends before my marriage came unravelled.

As we've hung out more and more, I've found that when hearing about the many travels she's had and of a few past experiences with old BFs, I've noticed that I've become more and more uncomfortable and insecure. Part of this insecurity is due to my lack of many partners. I've been with three (all fairly long-term.) Add to this, her age leads me to assume that she's had many partners and experiences with these guys.

My question is this, do you have any advise on how I might help myself become more comfortable with my worries/insecurity around her being more personally and sexually experienced?

I think this is girl is great, no bull****, no games. I would like to continue to see her.

Thanks Guys any thoughts or advice is really appreciated!

 

[Weak_Game]

Straight up. Ive gotten into sexual past with woman. Never ask if you can't handle the truth. No longer do i disclose how many sexual partners ive had nor am i curious as to her. I once freaked out when i found out my girl (an ex of many years ago) had over 100 and did porn. After i heard the truth. I could never handle it and we broke up due to my insecurities. I couldnt hand the truth. Before i knew the number we were great.

Don't ask don't tell. Its the best policy. Also try not to talk about x's or let her bring up hers. There is no need to compare or even share stories. Depends if you guys are comfortable with it. Sometimes its just too much information.

 

[NorthernSoul]

Don't ask don't tell. Its the best policy. Also try not to talk about x's or let her bring up hers. There is no need to compare or even share stories. Depends if you guys are comfortable with it. Sometimes its just too much information.

Thanks for the reply. I definitely agree with you. Unfortunately, seeing as we were friends before our relationship progressed, I have met a couple of her ex's and some of these conversations have come up. I'm hoping there some advise for that type of situation. Thanks.

 

[KarmaSutra]

Has she fvcked donkeys or shoved any small rodents up her chute? If it's just guys who have dumped loads in her you shouldn't worry.

Be grateful she's experienced with the c0ck and comfortable with an insecure schmoe like yourself.

 

[Francisco d'Anconia]

... her age leads me to assume that she's had many partners and experiences with these guys.

Stop scaring yourself and enjoy the fact that you are the guy that's with her now.

 

[Phyzzle]

This chick sound real classy, bringing up the old boyfriends.

Feel free to roll your eyes and say "yeah, yeah, enough about your old harem. What happened on that trip that didn't involve guys?"

 

[Latinoman]

Early in the relationship you should NOT have "feelings". In fact, you should be 100% rational and logical. This is when they tend to open up and confess all their indiscretions. Later, when they figure out you have issues with this kind of behavior, then tend to cover up.

What does this do for you? It give you an idea of the quality of this woman and if it is worth pursuing as a VERY LONG TERM RELATIONSHIP.

When it comes to a woman past...I care. Because that past would determine what is the POTENTIAL future with her. And allows me to prepare myself mentally (just fun vs. long term relationship but no marriage vs. possible marriage material). You see? I don't think about the real future, I only think about "potential".

Here are the things I care about when it comes to past:

1- One night stands

2- Divorces (and why - abuse? cheating and who? etc.)

3- Drunk girl (I avoid those as SERIOUS relationship at all cost)

4- Group sex or threesomes

5- lesbianism

6- the monkey syndrome such as going from ravine to ravine (or holding to a boyfriend until finding another)

7- Cheating (based on MY definition of cheating)

8- Number of cancelled engagements

Some things I might ask straight up...others, I can deduct by listening to the woman opening her mouth.

Now...would that disqualify a woman? Nope. I would simply allowed me to "qualified" her.

IMPORTANT!
Another thing...and this is important...older women (5+ year older than the man and 35+ years of age) would apply the trick to MAKE ANY SECURE man insecure. That's one of their two main weapons...the second weapon is sex. It happens to the best of us. And I bet she is playing that trick on you.

 

[Sinistar]

NorthernSoul would you believe that sometimes we seek help that we aren't really aware we are seeking? If not, why not just skip this response.

I'm 28, recently divorced and dating a 35 year old

I'm admitedly not a fan of not dating 'older' women and at +7yrs I immediately categorized you in this lot. More importantly, the first thing I wondered was how you met and how long you knew each other before starting to date. Viola, you answered that question for us

With some help from SoSuave and some confidence, I've been able to hook up with this attractive, experienced woman I work with. This particular relationship started as we were friends before my marriage came unravelled

Now here's what I read. You have placed a higher value on her than yourself (and this will become more obvious with what you write later). To start with you are trying to qualify her to peers (ie she's attractive & experienced). And you tell us how the relationship started (ie friends first before divorce). So why then did you volunteer that information when your question is really simply in regards to insecurities regarding women with more experience? Hmm...interesting.

I've found that when hearing about the many travels she's had and of a few past experiences with old BFs, I've noticed that I've become more and more uncomfortable and insecure. Part of this insecurity is due to my lack of many partners. I've been with three (all fairly long-term.) Add to this, her age leads me to assume that she's had many partners and experiences with these guys.

Ask yourself this question. Let's say you had previously bedded 100 fine HB's in the course of your life and then you find yourself comtemplating a relationship with this woman. Do you really think that extensive se#ual experience would have prevented this twang of concern? Or is your real concern something deeper, more related to her past, her choices, your compatibility and an uncomfortable feeling that she is in control of the relationship?

My question is this, do you have any advise on how I might help myself become more comfortable with my worries/insecurity around her being more personally and sexually experienced?

The answer to this question is quite simple. Date and be intimate with more women.

I think this is girl is great, no bull****, no games. I would like to continue to see her.

I think this where you are hinting at the real question. I think what you are really asking is "Guys something ain't right here, heck even I know I wouldn't have posted if it 'felt' right. I'm wondering what I should do now?"

Okay my friend, I went a little deep on you. Here's my basis. Quite often, an older woman will latch onto a younger guy. They play it safe, gain the control frame and eventually 'something just don't feel right.' While they relish in their (albiet) unhealthy acquisition of control & ego boosting, negative AFC crap (ie doubt and insecurity) are the outcome of this unbalanced interpersonal relationship equation. I have a suspicion that this is what lead you to post. He11 this very type of scenario has affected many of us. Unfortunately it usually winds up in the guy gettin' his emotional arse kicked. And woman have a 'insecurity radar'. You're telling us about your insecurity no doubt lags the fact she has probably already perceived it. When she received that strong of a signal it implicitly places in her a Alpha state which can be quite difficult to overcome.

My advice. Look for (or force yourself to 'see') any red flags. For example, dating a co-worker can be tricky. Is her past se#ual history intimidating you or is really tripping your gut that something isn't right. Does she have a healthy group of female friends or does she only have male friends. Is her family decent, stable, etc. And what about those past relationships. Establishing a quasi-friendship first is a great way for woman to get a man to look past many of these big red flags.

On the other hand. If you can truly say you have little or no emotional investment, follow $FD's advice, don't get to wrapped up in this and enjoy the time together.

 

[NorthernSoul]

Thanks for the post. I realize I'm acting AFC...

Here are the things I care about when it comes to past:

1- One night stands

2- Divorces (and why - abuse? cheating and who? etc.)

3- Drunk girl (I avoid those as SERIOUS relationship at all cost)

4- Group sex or threesomes

5- lesbianism

6- the monkey syndrome such as going from ravine to ravine (or holding to a boyfriend until finding another)

7- Cheating (based on MY definition of cheating)

8- Number of cancelled engagements

To your items above, the only ones I could see as possibilities (though my guts tells me differently) would be:

#1-One night stands
I don't feel she's the type to be much into one night stands, but perhaps I'm being naive. Shortly before we had sex the first time, she had said something to the effect that she never moves this fast (5 dates) and that she's not slutty. (I'm sure you guys will have a response to this )

#3-Drunk girl
There were two periods in her life where I can see her partying a lot coming into play. 1) Right after college she went clubbing a lot with her a gay guy friend of hers, whom I've met and is very gay. 2) After she broke up with her serious boyfriend of 7 years, whom she lived with.

I'm not sure if these mean anything, but I guess that uncertainty is what makes my imagination wonder.

IMPORTANT!
Another thing...and this is important...older women (5+ year older than the man and 35+ years of age) would apply the trick to MAKE ANY SECURE man insecure. That's one of their two main weapons...the second weapon is sex. It happens to the best of us. And I bet she is playing that trick on you.

You mentioned two tricks. I only understood one from your post.

Perhaps I approach this with situation with great confidence and bring NONE of these concerns of mine up. I haven't up to this point.

 

[NorthernSoul]

Now here's what I read. You have placed a higher value on her than yourself (and this will become more obvious with what you write later). To start with you are trying to qualify her to peers (ie she's attractive & experienced). And you tell us how the relationship started (ie friends first before divorce). So why then did you volunteer that information when your question is really simply in regards to insecurities regarding women with more experience? Hmm...interesting.

I guess I was trying to give some background on her, in case that would lend any insight. (e.g. Her being smart and educated, rather than a high school dropout who lives in a trailer park. Know what I mean??)

Ask yourself this question. Let's say you had previously bedded 100 fine HB's in the course of your life and then you find yourself comtemplating a relationship with this woman. Do you really think that extensive se#ual experience would have prevented this twang of concern? Or is your real concern something deeper, more related to her past, her choices, your compatibility and an uncomfortable feeling that she is in control of the relationship?

I'm sure what you say is possible, but I do feel we are compatible and that she's of good moral character. In regards to the control of the relationship, I feel like this insecurity I have is giving her some of that control. I don't know that it's intentional on her part, as she's not overtly waving her past in my face.

Okay my friend, I went a little deep on you. Here's my basis. Quite often, an older woman will latch onto a younger guy.

She had dated a few guys significantly younger than her. Are you meaning that she's getting off on the control? Or just wants to be in control of the relationship? Any thoughts on how to counteract? Confidence and Indifference?

Does she have a healthy group of female friends or does she only have male friends. Is her family decent, stable, etc. And what about those past relationships. Establishing a quasi-friendship first is a great way for woman to get a man to look past many of these big red flags.

Yes on the GFs and family, no to the GuyFriends. She seems balanced enough. I will look for red flags. Any specifically I should look for?

THANKS SO MUCH!

 

[Sinistar]

NorthernSoul,

Your response was quite a refreshing change, instead of an ******dly spiraling response filled with more rationalizations, you remained quite calm.

[x] - on the smart and educated vs high school dropout in the trailer park.
[x] - on the good moral character.
[x] - on feeling compatible.
[x] - on having female friends
[x] - on coming from a decent family.
[x] - on not having a stable a beta male friends.

From your response I will change my tune a bit because maybe this is a case where a hook up with an older HB will be a positive experience for you. My advice, start living within a simple reframe (and thus your frame). It goes like this. From the instant you read this, see her in your mind as less mature than you and thus you are in charge.

An example. If she were 23 and threw you a couple nasty sh!t tests or lied or dissed you, would you take it - he11 no. For some reason it is often easier to see this for what it is and take healthy actions when they seem 'less mature'. However, when she's older (as in your case) you might be hesitant to call her on her sh!t and bingo, she's got you by the ba11s. So just set and keep the frame that you bring the maturity to the equation. Besides, in the end she's just a plain old common female, same emotional crap, etc.

You asked about Red Flags. Well, given your comfort level with her, I wouldn't advise spending every minute looking for something wrong. Just always be 'aware' instead of living inside their programmed reality.

What would I watch for with an older woman? Does she have an extensive dating history with younger guys, if so you are more likely to replaced when the high wears off. Be more aware of the things that silently trash a relationship such as anonymity and half truths. Women who've been through bad STRs/LTR's tend to sh!t test more often, too much of this is not acceptable. Run a sanity check, is this older HB reciprocating (compare it to the way your ex reciprocated when things were going well between you - this should be as good or better right?). And monitor yourself! By this I mean specifically make sure you are not trying to save her because she is older and single and expect the typical fantasy of younger guy finds older babe to achieve amazing se#. Remember, when you are 50yrs old she will be 57. You do the biology homework on that one. Now run the numbers again with her being 7yrs younger, heck you'd be 50 and still getting the good stuff for years to come.

Are you meaning that she's getting off on the control? Or just wants to be in control of the relationship?

Duh to both! They love 'getting' control. And they want to know that they can break a dude and get him to SUPPLICATE The irony, once they the get the control they know its not right, things suck and they move on.

She brings her past with her to this relationship. To blindly say "It's in the past" and forget about it is being naive. Relax and enjoy the time NOW with her. Either she will prove she's decent through actions, reciprocation, trust, honesty etc. Or she might slowly reveal a negative side if she is the type to get bored or take the relationship for granted.

 

[azanon]

My question is this, do you have any advise on how I might help myself become more comfortable with my worries/insecurity around her being more personally and sexually experienced?

2 things, both involve transforming your mind:

1. Instead of seeing that as a reason to be insecure, i would think wow this is a neat opportunity for me to learn from a woman that knows more about sex than I do. Focus on the fact that you're gaining, instead of her potential letdown.

2. Second, if you're 28 and she's 35, its actually HER that should be doing the worrying. SHE is getting to have BOTH a younger man and one less "tainted" by multiple women instead of you being more middle aged wtih some long sexual history. She's thinking a 28 year old is less set in his ways and maybe you're still trainable.

Think of it like this... what would you rather have, a "near" virgin 28 year old, or a 35 year old that's been around the block a million times. The higher value is the former, not the latter. Its no different with men (provided you have good means to take care of her).

 

[decades]

I would tread carefully here very carefully. first off this is someone you work with. that's a big no no. second she is older. no that isn't always bad but its somewhat of a red flag in my book. so you have two red flags to watch. She also said "I never do this before". That is a red flag to me. I heard it and I now think its a lie they say to not look like a bad girl.

The other thing I noticed is that your gut feels insecure. I have learned to pay attention to that. I have been with women where I felt that and women where I haven't. And what I noticed when I did was there was a reason I felt it. And I tried to figure it out and what I was hearing was what was called "jealousy making".

Many women out there get a some kind of charge out of making their partner jealous. its a "needy" thing. Now its unclear if she is doing this but it can be very subtle.

The bottom line is I would not get oneitis with her. My hunch is that this is not going to lead to white picket fences and 1.9 kids. Be very very careful as you have big potential to get "caught up" in this and get oneitis and get a nasty HURT when it all falls apart. The age thing the work thing and the "gut" thing make me say, take it very very slow!!

regards

 

[Latinoman]

You mentioned two tricks. I only understood one from your post.

Perhaps I approach this with situation with great confidence and bring NONE of these concerns of mine up. I haven't up to this point.

Two tricks...(they might not be intentional).


1) Sex. She will probably give you lot of it...until you get addicted. But be ready for the "all you want is sex" or any other guilt trip such as "can we just hold each other"? Also remember...when you turn 38 (and by looking at things, I wouldn't be surprise if you fall so hard for her as to consider marrying her) she will be near her Menopause ages where her libido might go lower.


2) Make you insecure. This can be done by telling you stories about her past (such as dumping boyfriends, or having men go crazy for her, or telling you stories that can get you insecure -e.g. sexual in nature) or her present (telling you when a man approaches her, etc.) or even future (telling you that she is comfortable beeing alone, or that she truly doesn't need a man).

Trust me...those are things designed to "qualify" herself (as the PRIZE) and at the same time make you insecure. And a woman that is older than you...which has slept with men that are OLDER (and even as young) than your current age...knows very well what might get a man into an insecure mode.

Women are VERY GOOD at perceiving men weaknesses...no matter how much we try to cover that stuff.

Trust me on that. I know. But my advantage is that I am aware of all this, so if it ever happened to me, I can take control of everything back...if I'm lucky.

 

[Latinoman]

She had dated a few guys significantly younger than her. Are you meaning that she's getting off on the control? Or just wants to be in control of the relationship? Any thoughts on how to counteract? Confidence and Indifference?

Hmmmm...I'm not an expert on this. After, I'm basing this on observation based on what I have seen for YEARS!

Typically a woman that does that is for a number of reasons:

1) She is VERY insecure and need to validate herself by being with men considerably younger than her.

2) She is VERY insecure and knows she can control men considerably younger than her. And she can do that by applying one of the two tricks.

3) She has some issues that a more established and mature man (with options) can detect. Therefore, she is already put in the shelf by those men.

4) She is a woman that has her self esteem tarnished because of a long relationship that ended it or divorce.

Think about this...



1) Sexual prime is not define by age (nope, NOT define by age)...and more by health, fitness, and ability to satisfy a woman. Men might lost some testosterene, but a healthy/fit mature man is as good (or better) than an average younger man. Mature women know that. And SHE knows that. (Add viagra into the equation and this has become a moot point)

2) Men professional and economical prime start hitting them in their 30s/40s.

3) Men social status is at his best when they are in their 30s/40s...because they are considered young and succesful.

So, why if she is all those wonderful things you described...why she is not dating those FIT, HEALTHY, ESTABLISHED, EXPERIENCE, ATTRACTIVE men that are in their mid 30s and 40s. I would tell you why...because a DJ in that age group has choices. And she is not one of them.

And if a woman has a choice between an AFC that is 38 and one that is 28...she will pick the one that is 28 (unless the one that is 38 is Rich!). But she will never pick a DJ that is 28 over a DJ that is 38.

 

[Sinistar]

So, why if she is all those wonderful things you described...why she is not dating those FIT, HEALTHY, ESTABLISHED, EXPERIENCE, ATTRACTIVE men that are in their mid 30s and 40s. I would tell you why...because a DJ in that age group has choices. And she is not one of them.

As much as I'd like to think he's found the rare case of an older woman being a positive experience in his life, I think these words from Latinoman are the money shot.

 

[resilient]

1) She is VERY insecure and need to validate herself by being with men considerably younger than her.

Wow.. I never understood why some women prefer younger AFCs, that makes perfect sense. They are obsessed with control. Great post!

 

[NorthernSoul]

Thanks

Thanks guys. All these posts are great. Much of what you've said has put this into great perspective. I think I'm going to play this one by ear and at the least just enjoy it for what it's worth.

I do think that for the most part she is a positive influence for me and that much of the issue lies in my insecurities. That said, your comments about her being significantly older and therefore not still as sexually interested at that age, make for a good case to not get too serious.

I'll be keeping my awareness up for some of those red flags and whatnot. I'll keep you posted and write some more in a week or so. I hope you can still continue to shed light on this.

Thanks again, you guys are awesome!