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Moral Dilemma - There is this woman, I will call her "Jill" (not her real name). XWW and I were mutual friends with her for years while married. She works with XWW. Jill and I would always chat via text now and then about a mutual interest in the same type of music, nothing more. Always friends.

When XWW and I first split, I was very open and honest that I was still talking via text with Jill. XWW asked, out of respect that Jill was now an administrator at her employer (and the school where our kids attend), and her own friendship with Jill, that I not push the friendship further than that, and I agreed, and communicated that to Jill. Everyone seemed happy.

For the last several months we have exchanged a few texts a day, mostly just about day to day life, and music, etc. Much like I would with any other friend. It has never been about XWW or her job, etc. But the friendship has definitely increased to more than just music, etc. We have never met in person, other than running into each other while I pick the kids up at school.

Now, Jill seems to be wanting to push our friendship further (possibly romantic? maybe, I get the sense). I like Jill, she is a wonderful person and someone that I could definitely see myself dating, but given her position as an administrator at my XWW's employer and my children's school, I feel it would be much too complicated to even attempt. It would impact my relationship with XWW, which is vital to the well-being of my children and my access/relationship with them.

Up to this point I have skirted around Jill's attempts to meet up in person, and brushed off her texts that strongly hint at attraction, etc. But she has not backed off or gotten the hint that this just isn't the right time. Not to mention, I have told her several times via text that recovering from this D is going to take a lot of time, and dating is a ways off.

So do I cut off this friendship? Or do I wait and see if she backs off of the romantic stuff? I feel like her actions are pushing things to a breaking point, and putting me into a difficult spot, and to be honest with all I have going, I am feeling kinda resentful toward her for putting me into this position. But my other concern is that I have this great woman interested in me, and I won't be able to pursue it because I am worried about my relationship with XWW. Should I be worried about that?

I am mostly just venting and writing things out, but any input from an outside party would be welcome. Thanks.

Gently here, but it sounds like your words "It is too complicated" and your actions of texting a few times every day are sending a mixed signal. You may think you are just treating her like a friend, but it sounds like she sees it/wants it to be more and may be picking up hints of this from you. It is flattering to be thought of in this way, but it is a slippery slope.

Quit with the subtlety. Tell her again what you told her at the beginning of your split; "You are a lovely person, I appreciate our friendship, but pursuing a relationship with you would cause too much conflict." You will probably have to stop the texting friendship. Remember, when you are ready to date there will be plenty of other lovely women who won't complicate the relationship you have with the mother of your children. It sucks, but you know what you need to do.

Thanks better,

That is exactly what I came on here to hear. I knew what I needed to do, but when you become so deeply engrossed in a situation, it is hard to see clearly sometimes. It is hard, because I do like this person, but in the fallout of trying a relationship, the only ones that could get hurt would be the kids. Not a risk I am willing to take. But I am to blame, it felt good talking with her, confiding in her, etc. but I clearly let things get further than I should have, given her position, etc. and now I have to hurt a nice person.

Just goes to show, even 10 months out from our split, which feels like an eternity, there are still so many emotions, and it is hard to trust your own judgment. This board is a lifesaver.

Sometimes head vs. heart is a tough decision to make, but it's one of those things that needs to be done consciously, because it's not just going to happen by chance.

Sometimes you choose to take the logical "right" choice, and sometimes you say "to hell with logic" and follow your heart and hope it leads you right.

Your ex should not have an opinion about who you date. You two no longer have a relationship, so she has to suck it up and let you live your life like the rest of us. If it is the friendship she is trying to preserve, and she doesn’t want her friends dating her ex, she needs to take that up with her friends, not you. If they can’t communicate about it, they mustn’t be that great of friends.

If you are honestly not ready to date yet, leave the ex’s feelings out of it and tell her the truth.

Just curious though, if the texts have only been of a friendly nature, why does meeting up have to be a date? I would find it odd if my friends never wanted to get together.

Up until about two weeks ago the texts were strictly friendly, then her tone changed to suggest something more. Then she started to push for in person meetings.

If this was strictly about dating one of my exs friends it wouldn't be so complicated. She really hasn't maintained a friendship with Jill. They speak occasionally, etc.

It is a few factors. 1 - she is essentially my ex's boss. 2 - she is an administrator at the school my children attend. 3 - I am not sure if I'm ready to date (which means I am probably not).

Take out the fact that they work together and I would simply tell her I am not ready to date - yet - but we could stay friends and go from there. However, they do work together, and my kids are involved, so the question is would I ever be able to date her?

My concern is that I am making this too complicated, as I have that tendency. I do have feelings for this person, and all complications aside, I would explore them when I felt ready. But given the complications....my kids are so so important.

Then she started to push for in person meetings.

No offense, but um, yes of course she wants to meet. Who wants a text buddy? The most superficial, no commitment, no strings attached kind of relationship there can be ... it's not even pen pal status.

The only kind of person who'd want that would be someone recently divorced, not healed from a D, or someone uninterested in who they are texting.

I hope I'm not being too snarky with you. But I don't see a moral dilemma here. I see a woman texting a guy hoping, and the guy really ought to just say, "I don't want a relationship with you sorry" and let the whole thing go.

Ok. Thank you for your honesty. You are right, I am overcomplicating the dilemma. Let me rephrase.

The relationship has hit a point where it is time to move beyond texting and into a real friendship or romantic relationship. Either way, would this be morally acceptable given her position as my XWW's superior and my children's school administrator, as well as my XWW's objections and the impact it would have on my relationship with her?

Either way, would this be morally acceptable given her position as my XWW's superior and my children's school administrator, as well as my XWW's objections and the impact it would have on my relationship with her?

No.

This is more of an issue of you not being ready than anything.

I think when you are further removed from your marriage, you'll see that who you date, when and how isn't anyone's business except between the two of you.

Politely tell her the timing right now isn't good for you so that she can move on.

AJ's MOM

I wouldn't date my X's boss, a friend of my X's or someone that has authority over my kids.

If it worked out between you, it could make things very hard on your X and maybe your kids. If it doesn't work out, it would probably make things very hard on you and your family depending on how she handlesit.

There are hundreds of women out there that you could choose to date, why choose one so close to home?

I see the fact that she is the administrator at your child's school and the fact that you admit you're really not ready to date as factors because those things directly affect your relationship/friendship with her and your family (i.e., your children).

However, I do not see your ex's opinion/desires as a factor at all. She certainly wasn't worried about your opinion/desires or the relationship between the two of you when she had an affair.

When you're further along in your healing and you're closer to indifference I think you'll see that you owe your ex no explanations at all about how you live your life.

For now though I think the only "right" thing to do in this situation is to be honest and tell this woman that you're not ready for any type of relationship between the two of you and then let it go.

If it doesn't work out, it would probably make things very hard on you and your family depending on how she handlesit.

Not to get you paranoid @traildad, but, depending on the type of person Jill is, she can also make things hard, if you reject her proposal. Subtle is the key word here.

Your ex should not be bothered about who you meet or not. Most often exs have a problem when the person whom they left behind moves on. It's unsettling to them. They simply cannot digest the fact that you can have a better life w/o them.

The only reason you should not persue Jill is that you are not ready.

That said, maybe you'll be ready after you meet her. It can click. You'll start feeling better, out of the mess WW created for you. It can happen.

When I split from my college GF, it was very very painful. At that time, I had a girl who was perusing me to the T. She was very very sweet. I was happy being with her as a friend. She was very bubbly and exciting. But, I was not ready. I was silly enough to talk to my Jill about my exGF, whom I missed. Being with my jill left the bad memories behind, albeit momentarily.

Ultimately it got my Jill uninterseted, as, I couldn't get over my break up with my exGF.

So telling Jill in a subtle way that your memories of you ex can possibly ruin a good prospect and you need more time. And you need more time. That's the safest way to turn Jill down for now.

Just my 2 cents.

It is a few factors. 1 - she is essentially my ex's boss. 2 - she is an administrator at the school my children attend. 3 - I am not sure if I'm ready to date (which means I am probably not).

You've answered your own question with these three things. High potential for drama with all of them. Is that really what you want right now, if ever? IMO, time to remind her that you are not ready for a relationship, and perhaps let the texting go, unless or until you're ready for more (including possible drama).

Hi,

I am engaged to an elementary school administrator and we actually talked about this early on. We met through Match and I had asked him, being male and in a profession where surely he met loads of single women (mom’s, teachers, aids) why he went to OLD to meet people and for the simple reason alone that it was not ethically right. No way would he get involved with a subordinate, so anyone in the building or even school system he felt was out, and a students’ mother would be really sketchy. Just way too much to lose.

Taken from the angle “what if it doesn’t work out?” there is just so much that could go wrong. You could just pray if it didn’t work it would be very adult with no hurt feelings/bad behavior at the end by the one who is the “dumpee” (the one who may not want it to end). Then think of all the personal information you each know about one another (again, hopefully it would be mutual in the ending!). What about when you have times you come face to face with this person at your childs’ school? How uncomfortable will that be? Not to mention the whole fact she is your WW’s boss. Even if you take away the fact of her being your WW’s boss, why not wait until your children are not in the building with her. It does lack professionalism in a lot of ways.

You sound really apprehensive which just screams to the rest of us you probably are not ready (which you so wisely already admit, Good for you!!!!!!), and/or think it is not right morally. So if you need an out just let her know maybe when the kids are out of the building. In the mean time it would probably be good for you to stop the communication (texting) because it does send her mixed messages. I had someone do that to me last year and really, it was a shitty thing for him to do. He lead me on and kept me as an “option” I felt (he was getting out of his marriage and had been a BS). Turned into dating others while he still lead me on (though he would stop while he dated then come right back). Ultimately the person it hurt the most was my finace (now, not at the time) when he re-appeared again, not to mention all the time it was messing with my head pretty badly. Not worth it and it is easy to use her as a “fall-back” to know someone might be there.

If it we me in that situation, I would walk away. And I mean totally cut it off because you know she has feelings probably beyond friendship. If it is meant to be, or you are really right for one another, it will work out when the timing is better, you are in a good spot and maybe your kids are out of the building. If there is a lot of time in-between then I would be able to over-look the fact she is your WW’s boss (who knows maybe one or both will have moved on by then anyhow so it might resolve itself.)

Yes, very wise advice here. I am definitely not ready, and ultimately that was driving my apprehension. It just shows how difficult this path to recovery can be. Lined with pitfalls. Had there not been the conflict of interest I very well may have, in a weak moment, entered into a relationship I wasn't ready for. I am thankful there was that added layer of complexity that gave me pause.

I communicated to her last night these feelings. Lesson learned. Moving forward.

Time to refocus on my most important mission - raising my kids. I lost focus for a few weeks, and that bugs me. I am happiest when focused on that task, and so are the kids.

Thanks everyone.