I(32m) am in love with my former sister inlaw(27f)

A man finds himself falling in love with his former sister-in-law after years of close friendship, shared parenting, and mutual support through grief and hardship. Despite his feelings, he’s unsure how to navigate the situation, especially given her lingering love for her late husband and the complexities of family dynamics. Read his heartfelt story and the dilemma he’s seeking advice on below.

‘ I(32m) am in love with my former sister inlaw(27f)?’

TLDR at Bottom This will be a long post. I’m finally at a point where I can’t stand this anymore. I’ve been in love with this woman for a very long time, maybe a couple of years at this point and I’m not sure if I should just kill it or attempt to make something with her. I met my ex-wife, her sister, when I was 23-years-old and the relationship developed very quickly and by 26 I had my son and daugther and had gotten married.

However, within months of being married my ex-wife had an affair, but worse than that the man she cheated with had gotten her into H***in. After confronting her on this she said she was going to get help, but instead she left in the night. I haven’t heard from her in 4 years and last I’ve heard she’s still with that guy and are homeless in Las Vegas. Not sure how true that is, but being focused on holding it together for the kids, I really don’t have the time to chase her down, nor do I want to after what she pulled.

I ended up getting a divorce in absentia. I did however maintain a very positive relationship with my inlaws after the fact. Every other weekend my kids stay over with their grandparents on that side and they pretty much treat me like a son still, I still go to parties at Christmas and am reasonably liked by the family. Nobody talks about my ex anymore mainly to not worry my kids. My oldest, my son is very hurt by his mother leaving. He’s 9 now and I’ve had to get therapy for him after he told me he hoped his mother was dead. She had been getting verbally abusive toward the end which was when he was around 5 or 6.

Anyhow, in the year following my ex leaving, her sister and my her boyfriend had started coming around a lot to see the kids. They knew I worked a lot and would babysit and call it practice as they wanted to have children of their own. My kids love them and were spoiled by them, which I didn’t mind because we all needed a little positivity. They got married and were very in love. However, her husband was killed in a workplace accident shortly after the birth of their daughter.

It has been extremely rough and painful for everyone involved as one can imagine. I followed my Sil’s example and began to take her daughter to give her time to herself if things got too hard to deal with or she needed alone time. She’s been in grief counciling for a few years but she still wears her ring and has told me she can’t ever imagine dating again. I talk to her about him frequently and she’s gotten to a better place but she’s still very much in love with him, I can’t imagine that sort of pain.

Over the last two years we’ve been a more constant figure in each others lives. My kids love their aunt and I have her over for dinner a couple times a week. My daughter and her daughter have become close and love being around each other so they have sleepovers. I’ve moved on from my ex by this but the idea of dating possibly someone dangerous as their mother has kept me out of the dating scene.

I don’t know when it happened, but slowly I began to get soft on my SIL. She’s a great mom for what she’s had happen to her. She’s one of the sweetest people I know and her sense of humor always leaves me laughing and happy. Then I started realizing that I’m physically attracted to her. I’ve always felt kind guilty about it because her late husband was a good friend and since she’s obviously is still grieving, so I’ve kept it to myself.

Since Covid started we’ve been together a bit more because social distancing has had us lose contact with most other people. Nothing romantic has ever been discussed and I try not to flirt, but last week it was very late and after the kids went to bed I made us a few drinks, not enough to get drunk but she decided she’d rather spend the night, so I took my couch.

I woke up to breakfast this morning and the four of us felt like the sort of family I’ve always wanted. She even kissed my forehead which is not something she normally does. I still didn’t say anything, but after she left I found my son quietly playing with his toys in his room. He looked upset so I asked him if he was alright.

He tells me point blank in the way only a kid can that he wishes Sil was his mother. I sat down with him and asked him why he thought that way and he gave a whole bunch of reasons her being nice to him, that she never yells about anything. He likes seeing her at his grandparents and she draws pictures with him, which I didn’t know they did. By the end of it my heart that is already melting for this woman even more wound up.

When visiting dropping them off with their grandparents, I tried to breach the subject with her folks to kinda feel around how people would see. I made a joke about she and I acting like a married couple sometimes and they didn’t laugh and were kind of stand offish, friendly but either they know something or they disapprove.

It’s getting too hard for me to ignore or pretend it’s not getting to me. I’m in love with her. Either I’ve got to kill it and find some way not to think of her, or I have to find some sort of way to navigate through this situation and tell her everything. If anybody out there has any insight on how to approach a widow, especially one who was married to a friend, with this sort of intention I could really use your help. TLDR- Sil and I became close after my divorce to her sister and death of her husband. She’s great with my kids. I’m in love and don’t know how to proceed.

Here’s the feedback from the Reddit community:

angelliu −  Some thoughts: 1. Don’t make a joke of this to her. She’s fragile enough that it’ll feel in turns both threatening and confusing for her.

2. Clearly she’s happy with the arrangement you guys have, a sort of ersatz nuclear family which carries little emotional demands and high rewards for both of you ie your kids get the love and structure they need from two adults who care for them and each other sans the drama. Not to mention each of you playing Mum and Dad creates that polarity which enhances a possible attraction.

3. So I must ask this: Are you absolutely sure you’re in love with her as a woman? I mean, forget the convenience and comfort of it all- just her as an individual, would you have chosen her without all of this going on?

4. I ask because as soon as the shock wears off, she’s going to wonder if it’s that or if there’s real substance to your feelings. No one wants to feel like a stand in and it will confuse her in the sense that she’ll have to start questioning herself as to if this is something she wants in general ie dating again, if you’re what she wants or if you’re just convenient, all those feelings of disloyalty to her now gone husband will be A LOT of emotion for her to deal with.

5. Which brings me to your expectations. This is an “over the fullness of time” situation. Unlike your ex, her former husband has now been idealized for perpetuity. He will never do any wrong, he will never be less to her, and he will always reign first in her heart. A love halted before its time and shrouded in grief can become a safe space for someone – as at least she can always say, I was married once, I did have that once – and depending where she is in her grief, she may choose to stay there for a very long time and not go further.

Whereas you, whilst hurt by your ex’ betrayal, are probably thanking your lucky stars she peaced out – no one wants the chaos of addiction around their kids. So your grief is different, you were left behind due to human flaw, and have been much too busy caring for your children. So while you share the state of being abandoned, each of your grief is personal and different. You will forever be second to the man who’s gone before you and I hope you can accept that.

More to the point, you cannot launch this on her and expect a simple yes or no. That’s irresponsible. If you want to prove to her that you are the man she believes you are, you’re going to have to think steps ahead.

6. That means, you need to start getting more personal time with her without the pressure of a proposal to be romantic with each other. Declaring it poses an unnecessary immediacy when I don’t see a need – neither of you are rushing to date other people. You need time alone with her just to hang out and talk without the kids always around you. Don’t ask her out formally, just carefully position yourself by getting time together like maybe stopping by and dropping off her fave coffee.

There’s obviously some danger here of being friend zoned but the trick to that is not to allow her to treat you like a gf. Just short bursts of personal time with intentional acts of attention, like if it’s Mother’s Day get her flowers, then joke “I know you’re not my Mum, but I’m so impressed by how you are with the kids that I just had to get you this.” If that extends to a deeper conversation, say something like, “you being how you are makes me really think of who I should have in my life”.

Always leave it a bit short on details to give her a chance to pursue it or leave it. Then the next time just give her flowers for no reason. Now she will either suss that this is getting romantic and will show you if she’s uncomfortable with it, OR she’s going to start looking at you and going hmmmm.

7. Here’s why I suggest this: like it or not, you guys are actually good for your kids together. And the potential of losing that just because she’s not where you are romantically, or worse, she may react negatively out of panic, is well – not really something you want.
8. I agree with ppl saying don’t run it by your in laws. It’s not their concern right now and it may even be a non starter. Who knows right?

9. As more time passes you’ll be able to tell if she’s more open or not, and that’s when you go full court press. Even if she turns you down, you’ve gained enough information about her and how she feels about being romantically involved that you’ll likely be able to talk about your options together more comfortably.

10. Obviously, follow all caution not to be neutered in her eyes. A lot of that you can help by keeping the polarity electric, meaning do things that keep each of you in that state of awareness of your maleness vs her femaleness. I sound like a d**che but I don’t know how else to put it.

But here’s an ex. I know when a guy’s interested in me if he mentions how much he makes or does something overtly manly. Once I was on holiday in the Seychelles and the very married son of the pensione owner took one look at me and decided he would fling his shirt off and chop wood right in front of my breakfast window. I was literally a captive audience. I wasn’t going to pursue it by any stretch, but it was his version of hey babe. Like seriously he went through an entire tree trunk, it was amusing and flattering.

I wish you luck OP, I get where you’re coming from and I don’t think this is impossible. I just think you have to be very careful to see things from her perspective and walk that fine line between gentle and exciting. PS if this works I’ll expect an invite to the wedding.

Mabelisms −  Dude, don’t run it by your in-laws before running it by her. Talk to her and see if it would be something she’s in to – and crucially, if she says no, accept it and don’t let it hinder your relationship with her.

discoduck007 −  Wow that’s a lot you have all been through. I think the person who will help you navigate this is your SIL. Your inaws are processing all of this in their own way and it would be unlikely they would see things from your angle, at least not in the begining. My advise would be to tell her your feelings, or some lighter version of them.

Express your desire to continue having her in your life and your hope’s that with times continued healing that you two could become more. I would tell her you have infinite patience for her healing process and that there is no pressure for more unless/if she feels it is time. And above all I would tell her you want her as a part of your families life no matter what her feelings. (Unless that is too much for your heart) I hope you find your way through this and that you all find healing.

EbonyUmbreon −  No insight but I hope this is updated if something is said it happens. This might be the dreamer in me, but this sounds like a happy ending everyone(You, your son, and us Reddit readers. Can’t really speak for others in your life) wants. Best of luck!

[Reddit User] −  I’m not reading any of the other advice because I don’t want to read anything that will change my mind. I am so rooting for you! I hope with my whole soft fuzzy heart that this is what is meant to be for you! How beautiful if these tragic beginnings could lead to a solid, lovely, renewal! Best wishes to you, 0727, I am praying for a positive update in the near future!!

VioletSeraphim −  There has been a lot of tragedy and heart ache in both your life and hers. There is a possibility that getting together could go wrong, that you wouldn’t work out well as a couple and that would be so damaging for the family, especially the kids.
I do feel kissing you on the forehead is a sign, but also she’s still wearing the ring so she’s not quite ready yet.

I would find a time to tell her about your feelings but if you date, TAKE IT SLOWLY. Don’t pressure her and don’t tell your kids about it. Communicate with her and make sure both of you are comfortable with your relationship before telling anyone, especially your kids and her parents. From the sound of it, both of you seem like reasonable, caring people. It would be truly wonderful if you can turn the heartbreak and sadness both of you experienced into something beautiful that will last. But you have to be patient and go slowly.

sssuuuzzz −  Here’s the thing, I have absolutely no advice on this matter. But what I’m going to need you to do is GO FOR IT, then come back with an update. It will be the best thing to happen in 2020.

SFtechgirl −  This is a sweet story. It happens sometimes. I know an older couple who were friends and happily married to other people for years. When both of their spouses died, they started hanging out and fell in love. They’re very happy together.

wild4wonderful −  Another stranger hoping for a good update today.

taranathesmurf −  Historically you two getting married would have not only been acceptable it would have been the norm and even the law. However now it might be considered well outside the norm. I would test the waters with her and if she is receptive try dating, then perhaps combining your households. Let your in-laws and the rest of society get used to it.