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New Relationship Off A Breakup


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I started dating a woman about 3 months ago.  We're both in our 30's. It's been awhile since I've been in a relationship.  I like her a lot but potentially there are red flags.  She was with her last bf for 9 years. They broke up in Sept and she moved out in Nov. We first went out early December. I don't expect her to be over him completely  but need to know that she is ready to move past it. When we initially started dating she was having her ex watch her kitten when going out with me. She stopped that anymore but were going on a trip. I think she will ask him again. She also wanted to borrow something from him for our trip but told her i would just buy one.  A month ago she has old pictures of them sitting out. I ask if that was him and she says yes and that she is thinking of cutting out to keep the pictures.  I also found out, not from her, that he is 20 years older than her. We're 2 years apart.  I don't have any moral objection to it but it makes me question the dynamic of their relationship and how healthy it actually was.

Most girls in their 20s are dating men in their mid 40s. I know she was with him for 9 years and he never asked her to marry him. I don't know if I'm walking into something that isn't going to work out and don't even know if it is something I can bring up to her.  If anything I want to prop her up and not make her shell up.

Edited by Tom224
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Did she want to marry him? Did she propose to him?

I wouldn't be comfortable with the type of contact she still has with him.  Has she invited you two to meet? I don't think it's appropriate for him to be coming to her place when she's not there to take care of her kitten.  

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She wanted to marry him but I don't think she proposed or they were ever engaged.  She was bringing the kitten to his place to watch.  She says it's because the kitten is so young.  But it's a cat which is a self sufficient animal.  I don't think she is hooking up with but it's makes me think other things like she is looking for a reason for him to be in her life and or vice versa.

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Well no I can see her needing someone to cat sit especially a kitten - I've done so for my neighbor.  But why him? And she then interacts with him at his place, etc.  She can hire someone to come to her house and check in, change the litter box, feed kitty.  Yes, she is not looking for a reason -she affirmatively wants to remain in contact with him.  

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Well if you think about it... their 9 yrs and only been apart a very short time.

You've been seeing her for 12 weeks.. Why are you wanting to do a trip with her already? ( Is it a lengthy one- eg. flying a distance?).

I wouldn't be jumping so fast into something with someone who's still stuck dealing with a long-term recent ex 😕 . And sure as heck would not be wanting to take a trip with them yet.

Do you honestly feel that comfortable with her at this time?

I think you are questioning a few things now... think some more.

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He may be married or in the process of a divorce for all you know and that’s why they didn’t or couldn’t get married if that’s what she wanted. Do you know why their relationship ended? 

In any case, yes, the contact seems odd. I don’t think it’s enough time to process a break up regardless of age.

Her feelings for you may be genuine but she hasn’t really learned to be single or think about how to problem solve without the last ex on her mind. If there’s a problem, she turns to him and I can see why that would make any new partner wary.

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11 hours ago, Tom224 said:

Most girls in their 20s are dating men in their mid 40s.

What? That literally should have been your first sign of red flag. He finished school when she was born. Not to diss couples with big age difference between them, but that big difference is weird. It screams "daddy issues".

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Is she over him? Quite obviously, not.

She is still holding on, very much. All the signs are there, she's not ready to let him go completely.

It's up to you whether you want to date someone who isn't over their ex, or not.

But it's a red flag that you even decided to date someone who told you they had just broken up with someone else.

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Sounds like they are now just old friends. Of course there is an adjustment period and that may take over a year or so. They will both eventually move on with their lives. Not sure if it's right to be a part of the transition...it may cause problems, but it's up to you to decide what to do. 

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Well I opened up a can of worms.  She did ask the ex to watch the kitten. Why him when there are other options? She says she asked others but couldn't find anyone else. I suggested boarding her or paying a pet sitter. It's just a weekend trip. Leaving Friday and coming back Sunday so it would only be for 2 days. She also says she is dropping her off when he is at work and they won't see eachother. Idk know if that is the case but that doesn't really make me feel any better.

He broke up with her. She says he found someone else and never had any intention of getting remarried or specifically married to her. Just speculating but I think once she was no longer a hot 20 something year old she was no longer what he wanted and he played her. She also moved here with him from up north.  So she left her family, friends, gave up her career to be with an older guy who was never going to fulfill her life the way she hoped for.

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I'm not sure how this would work between the two of you. I'm so sorry. Do you mind me asking what you see in her or what keeps you from ending the relationship? Is it the companionship that's enjoyable or do you find her attractive and winsome in other ways? 

This part in your first post seems a little contradictory and I'm wondering if you can clarify this a bit more because it may be the crux of why you're torn at the moment. 

Quote

I don't expect her to be over him completely  but need to know that she is ready to move past it.

 

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2 minutes ago, Tom224 said:

Just speculating but I think once she was no longer a hot 20 something year old she was no longer what he wanted and he played her. She also moved here with him from up north.  So she left her family, friends, gave up her career to be with an older guy who was never going to fulfill her life the way she hoped for.

This is pretty harsh. Doesn't really sound like you respect her so much as pity her, which is about as rough on the foundation as her still being tangled up with her ex. 

If dating someone straight out of a relationship isn't for you—well, that's totally understandable. It's not for many, for the reasons you're learning: the questions, the doubts, the suspicions, the kittens—it can all cloud things in the fragile, early days of connection. But it's not as if she falsely advertised herself, so it's worth taking some personal accountability here. You were drawn to all this at some point, and that point was more or less yesterday. Did you see her as person, or as a problem you could solve? Regardless, there's really no need to start painting her with a shady brush. 

If you see a future here, but have some concerns, why don't you just talk to her openly? Ask her what kind of contact she's hoping to maintain with her ex, while making it clear you understand it's complicated, and then listen to what she says and how she responds. That way you're not sleuthing and ruminating and creating these indirect tests, but can instead know if you two are on the same page. Any way you cut it, this sort of navigation and negotiation is going to be par for the course in some way, shape, or form with her, or anyone, who was in a long relationship a few exhales before your first date. 

On the other hand, if this is just not for you, and you're realizing that as you become more invested, be honest with yourself, and with her, about that. That's okay. Many people, if not most, would not be game to roll the dice on someone so fresh out of something so long. Whether they're still in touch or "never speaking again," the embers are still simmering and the heat can singe newcomers and new connections. Time, and time alone, is what puts them out, so it's up to you to gauge whether you can be your true, open, and secure self as that time passes, and whether you can trust—or not—that she is sincerely ready for something new. 

8 minutes ago, Tom224 said:

So I guess she didn't try that hard or just went to him because it's convenient.

Again, this attitude and perspective doesn't serve anything. It's like you already believe she's deceiving you in some way, and are trying to prove that, when it seems that what has changed here is that you're more invested—and, therefore, more nervous about things than you were when dude was watching the kitten so you guys could go on the dates. 

Don't get me wrong. There's plenty to be hesitant about here. At the same time, there are people who navigate this stuff with grace. You've just got to be honest about your own threshold for what you've signed up for. What seems workable after a few dates, or a few months, often shows itself to be more complex as time passes.

Perhaps that's what's happening here, sad as it is to consider? 

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20 hours ago, Tom224 said:

I started dating a woman about 3 months ago.  We're both in our 30's. It's been awhile since I've been in a relationship.  I like her a lot but potentially there are red flags.  She was with her last bf for 9 years. They broke up in Sept and she moved out in Nov. We first went out early December. I don't expect her to be over him completely  but need to know that she is ready to move past it. When we initially started dating she was having her ex watch her kitten when going out with me. She stopped that anymore but were going on a trip. I think she will ask him again. She also wanted to borrow something from him for our trip but told her i would just buy one.  A month ago she has old pictures of them sitting out. I ask if that was him and she says yes and that she is thinking of cutting out to keep the pictures.  I also found out, not from her, that he is 20 years older than her. We're 2 years apart.  I don't have any moral objection to it but it makes me question the dynamic of their relationship and how healthy it actually was.

Most girls in their 20s are dating men in their mid 40s. I know she was with him for 9 years and he never asked her to marry him. I don't know if I'm walking into something that isn't going to work out and don't even know if it is something I can bring up to her.  If anything I want to prop her up and not make her shell up.

I think you need to be careful… in my opinion. You are in a situation where there’s a possibility her and the ex will end up back together. While it can be possible for ex’s to remain friends, this usually doesn’t happen for a long time after the breakup…. After feelings and emotions are sorted out. A few months isn’t enough time. In her case, they are still attached to each other… not just “being friends”. I think you’re best cutting her loose (for now) to sort things out for herself. You’re possibly a rebound. Honestly let her go now before you get hurt. She’s not ready for what you are ready for and she isn’t going to be able to give what you have to give. 

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1 hour ago, Tom224 said:

She did find someone else to watch the kitten. So I guess she didn't try that hard or just went to him because it's convenient.

No, she went to him because she wants to keep a connection to him. 

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1. How/where did you two meet?
2. Where is the new girl he's dating? She's okay w/his ex being in contact with him (kitten and all)?
3. HE broke up with HER. SHE still wanted/wants the rel'ship and MAY leave you, if he ever asks her back?

I feel like she's physically with you, but emotionally and mentally not. Understandably though, given the situation you described. There is defn'tly A LOT of baggage there. She uprooted her life for an older guy. He was either still married, or single - but does not wish to remarry(or like you said, not her)

What's your rel'ship like, other than this ex issue?

After all these months, if you still don't feel comfortable discussing her past, or yours, that's not healthy either. It sounds like you're walking on eggshells w/her.

How did the trip come about?

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A friend's gf works with her and set us up. Our first date lasted 4 hours and we both had a good time.  She pushed to keep seeing me and wanted to keep making plans to see eachother. I tried to slow things down knowing she was recently in a long relationship. She invited me on a 10 day trip to Europe during the summer.  I'm not able to take off the time because of family health issues but suggested doing a weekend getaway so we decided on that. 

Together I think we're great. There aren't many people I'm comfortable enough with to be myself but I feel like I can with her without judgement. I view her as a peer and an equal and hope she sees me the same. Im happy when im with her.  We have fun doing things together. She has opened about some things and when she has I only listen.

I don't really know anything about the ex's new girl.  She thinks he found her while still dating.  Maybe she cares that she still goes to him or maybe not. 

She tells me it's over between them and there is no chance of them getting back together.  I don't doubt her on this at all. She thinks he screwed up her life. She wanted to settle down, marry, and have kids. She gave up the job she wanted and the career she wanted.  He was previously married, already had kids, and didn't want that.

Maybe I'm wrong for thinking this but the possible dynamic of her last relationship is what concerns me. She was closer to his kids in age than the ex. From what she tells me her parents divorced when she was young and neither were supportive. By 12 she was the most mature person in either home.  I get the way I previously phrased it does sound harsh and the only things I know about it are from what she has told me and from pictures. 

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23 minutes ago, Tom224 said:

She thinks he screwed up her life. She wanted to settle down, marry, and have kids. She gave up the job she wanted and the career she wanted.  He was previously married, already had kids, and didn't want that.

That's odd.  When did she ask him about his intentions towards her and his goals about marriage and kids -did he lie to her for years and tell her he wanted that?  If not how is it his fault? I'd be careful with her version of events unless indeed he lied to her for years (and you believe that that is true).

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Posted (edited)

From what I know she wanted these things and questions why he would string her along if he never had any intentions of asking her.  She has a wedding dress in her closet so at some point they had to have discussed it. I don't think she would have one if they didn't. Did he buy it for her without proposing? Did she buy it thinking he would come around? Were they looking at getting married and other things happened?

Edited by Tom224
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5 minutes ago, Tom224 said:

From what I know she wanted these things and questions why he would string her along if he never had any intentions of asking her.  She has a wedding dress in her closet so at some point they had to have discussed it. I don't think she would have one if they didn't. Did he buy it for her without proposing? Did she buy it thinking he would come around? Were they looking at getting married and other things happened?

So it really depends on what exactly strung her along.  If she truly wanted those things - she'd have wanted concrete plans, answers, a wedding date, a kids timeline.  Especially since he'd been married before/was a dad. I'm a little wary of people who blame someone else if the writing is on the wall or they're staying for fear of being alone, or choosing to be in denial about the truth.

Also doesn't add up that she'd want him to cat sit if he screwed up her life.

Edited by Batya33
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Right, I don't disagree. I really think she went for him as the older man who would fix her problems and take care of her.  At some point she had to come to the realization he wasn't going to marry her prior to the 9 year. 

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14 minutes ago, Tom224 said:

Right, I don't disagree. I really think she went for him as the older man who would fix her problems and take care of her.  At some point she had to come to the realization he wasn't going to marry her prior to the 9 year. 

Yes.  So understand that past behavior is the best indicator of future behavior.  She chose to stay and now she is playing the victim in how she describes it to you. And still looking to him to cat sit/take care of her.  

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