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New Relationship Off A Breakup


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I honestly think you have two choices here:

1. You have a real, long, honest, difficult conversation about her rel'ship w/him. It's been long enough that you deserve that much. If for no other reason, than the doubts and concerns she raises in your rel'ship, and the ability for both of you to move on together (if the talk goes well and in both your best interests)

2. You take the back end route, go to your friend and his GF, and find out as much as you can. But, not sure this is the best option.

I know you have a weekend planned, so unless you can have this convo b4 then and be okay with the plans being ruined, or postponed, then I suppose wait until next week. But, she may be VERY upset if she finds out this was on your mind, b4 your trip.

I don't think she's a bad person, not at all. I think she's been through a lot, and thinks this is the way she should navigate the situation. But, you can't keep pushing for feelings aside to accommodate her and him. Your rel'ship should NOT involve 3 ppl.

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Posted (edited)

I think she is awesome but you're right she has been through a lot and has baggage. Once you're in your 30s you have to expect there to be some.  If we had met 9 years ago or even 1 year later things would be different.  There are times i look at her and see the person who is everything i want. Going to do my best to let it go for the weekend and just have fun with her.  At some point if we're going to continue to see eachother romantically this is a conversation we must have.  The last thing I want to do is make her shell up or defensive so that's going to be tough.  

Edited by Tom224
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When you become exclusive with someone, only do so if you are on the exact same page for dating/life goals, and relationship boundaries. 

Assuming you failed to do this, and I don't even know if you are exclusive, but regardless, it's time to have this discussion before you decide to move on with her or not.

Tell her exactly what you're happy with in relationship rules. And don't bend what you want, afraid you'll lose her if she doesn't agree. If you believe in zero contact with exes, that's quite reasonable since they don't share children. Don't think that you're a jerk for wanting that rule. My husband and I have that rule, unless it involves issues about our grown children, which ends up being rare.

Good luck and let us know how it goes.

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It’s not the everyone has baggage thing. Some do some don’t. Some 20 year olds do and 40 year olds do. Had a friend - self made woman - top of her profession by her late 20s- who was a homeless teenage mom. Baggage yes before she was 20.   Much more than even that. In her 50s now, wealthy retired grandmother married to a wonderful man with baggage too.  Depends what it is and whether it affects compatibility. Please don’t go with “but she’s my soul mate “ and “but I love her “. Take a blunt direct look at what she stands for and whether she’s aligned with you in values and goals. 

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12 minutes ago, Tom224 said:

I think she is awesome but you're right she has been through a lot and has baggage. Once you're in your 30s you have to expect there to be some.  If we had met 9 years ago or even 1 year later things would be different.  There are times i look at her and see the person who is everything i want. Going to do my best to let it go for the weekend and just have fun with her.  At some point if we're going to continue to see eachother romantically this is a conversation we must have.  The last thing I want to do is make her shell up or defensive so that's going to be tough.  

Watch your words, and how you approach her. This isn't SOME baggage. It's almost a decade of her most precious years. Not to mention, you said she's had no support from a very young age, and had to be the "adult" early on.

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3 hours ago, Tom224 said:

She tells me it's over between them and there is no chance of them getting back together.

I would believe that - but it's also beside the point. 

The point is that her heart and mind are clearly still with him. Regardless of whatever might happen (or not) between them in the future, it is very evident that she isn't over him. 

As such, I would not hold your breath for a serious relationship with her. She doesn't appear at all ready to let anyone else in since she hasn't fully let go of him. 

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3 minutes ago, Tom224 said:

Any suggestions on how best to approach her about this?

It's unrealistic to expect someone to heal rapidly in a short time span and still expect to date them so I think the heavy lifting will come from you and asking yourself whether you can be with someone who hadn't taken the time to heal from her past relationship.

She may tell you what you want to hear but the cold fact remains that she's just not ready for a relationship or isn't the person you're looking for. You can talk as much as you want or approach this or discuss this but it won't change your circumstances right now. 

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43 minutes ago, Tom224 said:

Any suggestions on how best to approach her about this?

What, exactly, is this that you want to approach her about? She's been up front with you about everything, and has already taken the steps you seemed to want when you began posting here: her ex is no longer watching the kitten, a choice she made with very little pushing from you. 

All in all, it sounds like you want her to do the impossible: to assure you that her past relationship is in the past, that it in no way poses a threat to what's developing between you two. But it's really just time that will provide the answers there, as is the case with every relationship in this early stage. So it's on you, as Rose said, to be honest with yourself about whether or not these are dice you're willing to keep rolling. Her path to healing is hers, not something you can expedite. 

In a way, whether she is genuinely "ready" or not doesn't matter if your reaction to all the variables is to become more skittish and hesitant. Generally speaking, this is why many people balk at exploring romance with someone fresh out of something: not just because said person might not be ready, or still raw, but because said person's circumstances make it hard to keep surrendering to the connection, as you're discovering.  

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2 hours ago, Tom224 said:

Any suggestions on how best to approach her about this?

About what, exactly?

You can see for yourself that he is still very much in her heart. Her reassurances that he is behind her will ring empty when you can see the writing on the wall this clearly. 

Invest at your own risk here, Tom. 

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2 hours ago, Tom224 said:

Any suggestions on how best to approach her about this?

What questions, concerns, needs, wants do you require answers to?  

What specifically do you need in order for you to move forward w/her?  

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On 3/8/2022 at 6:16 PM, Tom224 said:

I don't know if I'm walking into something that isn't going to work out

I think you probably are. You described so many things that would make me turn around and walk the other way. The very recent break up of her 9-year relationship. The ex watches her kitten. She wants to borrow something from the ex. She still looks at pictures of them together (I mean that's practically saying out loud that she's not over the relationship). It's a lot.

5 hours ago, Tom224 said:

Any suggestions on how best to approach her about this?

I don't know. You're not really stuck, but you might as well. You're kind of in it now-- I think it's going to hurt whether you do or you don't.

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Went on our weekend getaway. She found a friend who offered to watch the cat whenever and think she is getting comfortable leaving the cat at home if it's just for a few days. She is also painting her place without the help of the ex. 

We did a load of laundry to make use of the amenities. She got worked up over her ex telling her how to do laundry which has nothing to do with us. We also had a pretty in depth conversation about her past. She was in a physically and mentally abusive relationship with a guy 13 years older than her who had 2 children and a crazy ex who tried to press unfound charges against them more than once.  This started when she was 23. After getting out of that relationship she met her current ex. He is 20 years older than her and filled multiple roles as a father figure, best friend, and boyfriend. She says her family didn't like him because he took her away from them but I feel there is much more to it than that.  

From her side he was controlling but didn't go into detail. Im curious as to why he went for her? Did he want someone much younger, was it to boost his ego after getting divorce, is he closer to someone 20 years younger than him in maturity?

 I asked why she stayed if he wasn't going to fulfill her life the way she wanted.  She want kids, he already had 2 and didn't want more.  She wanted marriage and he didn't. In hindsight she agreed. They compromised on kids by saying she could raise puppies. What happened to the puppies because they never got them? They were engaged at one time but everytime they set a date he came up with an excuse. I don't know how long that or how often that went on. They were supposed to get married in 2019 but for whatever reason they did not.  Than covid came and they never got married. 

I told her there is another side to the story that I don't know. She stayed with him because she was content and didn't have a reason to leave him. I don't know.... In hindsight she doesn't know why she didn't leave him earlier and others have questioned her on this before.  Imo marriage and kids isn't something to compromise on in a healthy relationship.

Her family also isn't very keen on her wanting to jump into another relationship so soon. Supposedly that was not her plan until she met me. To her credit she has been very open with me and she is trying. I just didn't really start to piece together the full extent of things prior to the last couple of weeks 

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33 minutes ago, Tom224 said:

Her family also isn't very keen on her wanting to jump into another relationship so soon.

This is where you say, "Thank you for being up front with me. I've been thinking about this a lot too, and I agree. I think you're great, but t's not a good time for us to go any farther with this."

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20 minutes ago, Tom224 said:

She got worked up over her ex telling her how to do laundry which has nothing to do with us. We also had a pretty in depth conversation about her past.

Sounds like a barrel of laughs. I can't see why you're hooked. 😫 I'm more concerned about the kitten. Just because a kitten might survive if left with the litter box, food and water, doesn't mean you should just leave them for days without companionship. They are living animals who enjoy the comfort of being around humans, and water can be knocked over. Ants could get into the food and be inedible. I stayed home about a week after getting a new kitten. But shortly after that, one day when we got home from work, we found that she'd climbed up the cat tree, went on top of the kitchen counters and fell behind the refrigerator. I can't imagine the suffering she would've experienced if we'd left her for days to go have fun on vacation.

As for me, I dated for enjoyment, and having someone regularly bring up their ex like with the laundry remarks, wouldn't be enjoyable for me. It's important to find out in general why past relationships didn't work, but why go in to these in depth details? But now that they are out there, you can see that her decision making skills are very poor, including jumping into something new after a mere month of being in almost a decade relationship.

And now your decision making skills are up for debate as well for dating someone a measly month out of being with a partner for almost a decade. Yeah, the success rate for this situation seems dismal.

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On 3/8/2022 at 3:16 PM, 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 would be very cautious proceeding with this. Honestly the best way to start this relationship would be to utilize a relationship counselor off of the bat. I know that may seem silly, but either you sail forward into the storm and risk causing many other problems resentment etc, or you tell her you want to take a break until she's over him and risk her moving on without you, your best tactical decision imo would be to seek a couples counselor and hopefully it will allow you to keep your supportive energy so that it doesn't become resentment, and hopefully it allows her to move past him, and better understand why she kept that bridge open, and understand herself. 

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1 hour ago, Tom224 said:

Went on our weekend getaway. She found a friend who offered to watch the cat whenever and think she is getting comfortable leaving the cat at home if it's just for a few days. She is also painting her place without the help of the ex. 

We did a load of laundry to make use of the amenities. She got worked up over her ex telling her how to do laundry which has nothing to do with us. We also had a pretty in depth conversation about her past. She was in a physically and mentally abusive relationship with a guy 13 years older than her who had 2 children and a crazy ex who tried to press unfound charges against them more than once.  This started when she was 23. After getting out of that relationship she met her current ex. He is 20 years older than her and filled multiple roles as a father figure, best friend, and boyfriend. She says her family didn't like him because he took her away from them but I feel there is much more to it than that.  

From her side he was controlling but didn't go into detail. Im curious as to why he went for her? Did he want someone much younger, was it to boost his ego after getting divorce, is he closer to someone 20 years younger than him in maturity?

 I asked why she stayed if he wasn't going to fulfill her life the way she wanted.  She want kids, he already had 2 and didn't want more.  She wanted marriage and he didn't. In hindsight she agreed. They compromised on kids by saying she could raise puppies. What happened to the puppies because they never got them? They were engaged at one time but everytime they set a date he came up with an excuse. I don't know how long that or how often that went on. They were supposed to get married in 2019 but for whatever reason they did not.  Than covid came and they never got married. 

I told her there is another side to the story that I don't know. She stayed with him because she was content and didn't have a reason to leave him. I don't know.... In hindsight she doesn't know why she didn't leave him earlier and others have questioned her on this before.  Imo marriage and kids isn't something to compromise on in a healthy relationship.

Her family also isn't very keen on her wanting to jump into another relationship so soon. Supposedly that was not her plan until she met me. To her credit she has been very open with me and she is trying. I just didn't really start to piece together the full extent of things prior to the last couple of weeks 

WOW! Okay. That's a lot to unpack. I'm glad you were able to approach the situation, and that you were both able to still enjoy your weekend (I think?)
I don't know exactly how old she is, but she's done this twice now, with the same type of guy. She never healed from the 13yr one, then jumped into this last one 9yrs. She's def'n on a roller coaster, but numb (for lack of a better word) on how she's going through life.

Personally, I would try to separate the "us" right now, and either choose to be by her side as her friend, while she seeks help. Or, you walk away and let her get help on her own. She can't continue like this. It's not fair to her, to you, or any other potential partner. There are emotions and scars she needs to heal first.

Let her know there's no shame in getting help. Esp. when she's been abused.

Edited by Rox22
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2 hours ago, Tom224 said:

In hindsight she doesn't know why she didn't leave him earlier and others have questioned her on this before.

Again, daddy issues...

Often times persons who have a complicated relationship with parents seek similar patterns in their relationships. To her that pattern is seeking older guys and getting approval from them. Hence why she stayed even though he had no desire to marry her at all. Because for him it was just having a younger girl. He had kids that he probably got very young. He doesnt need more. It was her that needed all that. 

Again, kitten aside, there is way too much to unpack there. Starting from that she isnt nearly ready to date anyone with those issues.

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Sounds like a therapy session rather than a weekend away.  I think she's looking to you to comfort her, provide for her, protect her - she's not in a place to be an equal in a healthy adult romantic relationship.  She also wants a sounding board.  I'd cut my losses if I were you.

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Just because you're not twenty years older than her doesn't mean she isn't expecting you to parent her like her previous exes did.

She's looking to you as a replacement for her ex who she didn't want to break up with, not as an individual.

I would put money on, if her ex called wanting her back she'd leap at the chance.

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Posted (edited)

A quick update. Haven't seen her since we've gotten back. She started painting her condo by herself. Yesterday she wasn't feeling well (depression) so she spent most of the day in bed. Tonight she is supposed to be going to a concert.  She couldn't find anyone to go with her so she is planning on going alone.  I hope she does.  That makes me happy. Yesterday I asked if she was still planning on getting a tattoo because she previously mentioned this. Eventually she said so my next question was what are you planning on getting? She sends me a link to her pintrest account.  The first tat is a flower pattern with the words "if  there is another world he lives in bliss. If there is none he made the best of this". I asked her why the epithet and she said she just likes the flower and would not get the word and the quote is about God. Maybe I'm not being logical here but it's also an epithet for fondly remembering someone you lost. But he's dead was her response. Again maybe not being logical here but I don't believe she didn't know that.  She is too darn smart and has a masters in both history and language arts. The other tats were all artsy or nerdier things. Maybe it really is she just likes the design but there is a lot there.

Edited by Tom224
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What is it that you’re looking for in sharing the above? Confirmation that this tattoo is connected to what you already know: that she is deep in the throes of untangling herself from her last relationship? Or an argument that the tattoo is just a tattoo and that you’re overthinking? 

The impression your posts give me is that you are drawn to the drama of all this, that you find her and the situation more enticing the more you prove she’s sprung on him. Could it be that you’re not really emotionally available yourself, and so you find her emotional unavailability familiar, compelling, safe?

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