How do you tell your ex that you’re dating again?

I think that in order to truly get a sense of where I am right now, you need to know the back-story to my current relationship.

I separated from my wife almost two years ago (it’ll be two years in March). It was amicable…we still get along…it was just a situation where we ended up being two friends who happened to share a child together. Not quite the ’til death do us part scenario I was hoping for.  Then out of the blue late last year it happened…

November 23rd, 2008 at 10:07pm

That’s when a message popped into my Facebook inbox. A curious message was attached to a ‘friend request’. It was curious because it was from somebody I had never met before.  But I decided to add them as a friend for two reasons: 1) She said that we shared a mutual friend and that she read my blog a few times, and 2)I thought  she was really cute. So here’s what she sent to me:

Glad to see that my friend request wasn’t creepy. 🙂

Yes, I *do* worry about those kinds of things. heh

Nice.  So my response?


No…it wasn’t creepy at all.



Yes…I was flirting.  No…I didn’t really expect much of anything to come from it. But what came from it was a whirlwind romance where I have since been completely swept off of my feet.  Totally head-over-heels in love.  Feelings that I don’t remember having during my marriage…which is a scary thing to admit to myself yet still exciting because of the possibilities that lie ahead.

In the 18+ months since my separation, I had been through an emotional rollercoaster. I had attempted to date people online right after my separation in an effort to make myself feel better about myself…to make myself feel loved. When that only made me feel worse, I pretty much crawled into an emotional cave. While I was absolutely ready to move on by November 23rd, I really didn’t expect anything to happen.

I knew immediately there was a connection there. There was something that I had never had before. Honestly…something I never remembered feeling from any previous relationship.  We ended up having the most incredible first date either one of us had ever had (I’ll detail that later in another post) and it’s been an amazing adventure ever since.

The bottom line…just so that I don’t ramble on too much…is that I feel the same now about her as I did at the very beginning, only more. She’s amazing. She totally gets me…she totally makes me happy…and she’s totally worth the time and effort it takes (and will take going forward) to see each other in spite of the distance.  I don’t know where this is all going, but I’m crazy about this girl. I’m absolutely head over heels for her.  So what’s the problem?

I haven’t told my ex yet.

We had both agreed that if we started dating somebody that we’d let each other know…just because a new person in our lives would affect our son.  And now that I’ve got that somebody in my life that I’m hoping will become a very big part of my future, I’m searching for “the perfect time” to tell her.

I don’t know if I feel guilt…if I feel like I’ll hurt her feelings…if it will truly put a huge “THE END” sign to the marriage.  I’m not sure why I feel this way or why it’s so bloody difficult in trying to find a way to tell her.  She probably already knows.  I mean, we’ve both got mutual friends on Facebook and I’ve been listed as being “in a relationship” for a couple of weeks now…but that only makes me feel worse for not being able to tell her first.

Is it that big of a deal?  Am I worried about her feelings without good reason?  Should I really be that concerned about it?  Do I tell her in person?  Over the phone?  In an email?

I know I have to tell her very soon because Sunshine is going to come visit me for a week (she lives a few hours away and we only see each other one or two weekends a month at this point).  With that week will come her spending some more time with my son.  And then my daughter, Rugrat, is flying in from Toronto to spend a couple of weeks with me next month…and I want to introduce them.

BAH!!  Why am I so worked-up over this??  I should just drop Ankle Biter off on Wednesday night and say, “Listen…I’ve got something I need to tell you.”

Isn’t that the way it’s supposed to go?


11 thoughts on “How do you tell your ex that you’re dating again?

  1. I thought I’d change to the comments, twitter can’t answer lifes problems in 140 chars!!

    I’ve been through this, I totally feel your quandary!!

    I’m no expert, but I’d like to give you my opinion. (I maybe completely wrong here though, forgive me, I have only just found this site on this post so maybe I don’t know you so well yet)

    Right or wrong, it’s all relative… this new girl is a big difference from your previous monogamous relationship. you’re going dating after having a son with someone and now you’re back to being open to a new relationship, it feels like a BIG thing. but, seriously dude, it’s just dating! I know you say this new girl “gets you” and all is good but you haven’t made any plans (yet) to move to Florida and set up a whole new family with car, house, career et al. (I’m working on the assumption that you haven’t made plans yet!)

    you’re just dating! (I might have said that before). To anyone else except you, that’s how it’ll be seen, just two people who share a similar wavelength getting together to enjoy food and chat and company and open to possibly more.

    you’re open to it going further and who knows.. it could indeed. but, until it does go further you should just chill out.

    the biggest mistake I ever made was not taking the time to do it right after getting out of a long term serious commitment type relationship. Sometimes a change feels better, be wary of rebound. it’s a b*stard!

    I think you’ll be fine though because you say there’s honesty. keep that, work on that and if it doesn’t work out, it honestly didn’t work out and you’ll be free of guilt or worry.

    if it does work out and it’s based on honesty, then you don’t have to worry about a thing. it’ll take care of itself.

    you can tell your ex you’re seeing someone, you don’t have to make a big deal out of it.

    You sound like a good guy, but your ex is your ex now. sure she needs to know because of your shared son but until you know what you and your new girl have, you can’t really say anything more than you’re dating someone.

    I’m certain that you’ll look back on this time next year and chuckle to yourself.

    sorry for rambling on so much! I have so been where you’re at and wanted to save you some unnecessary heartache

    great blog btw!

  2. You need to tell her in person. Don’t just email her — that would not be a good choice. Yes, it will be awkward, but she needs to know if your kids are going to be around this person. And out of respect, she needs to her it from you, not from facebook. Will she be sad, probably. But it is a new beginning and she might just be happy for you. Either way, tell her asap.

    Just my .02,

  3. I think I’m going through what you went through with regards to dating during your separation. I tried the online dating thing shortly after the separation in the hopes that I could fill the emptiness and loneliness, but that didn’t work so now I’ve decided to just focus on me and my son right now and if something happens down the road, then it’ll happen.

    My soon-to-be ex and I have the same verbal agreement about dating other people, though I have the same trepidation as you seem to have – I’m not looking forward to giving or receiving that news. Mainly because I fear another man appearing in a father-figure role to my son. That will really bother me.

    That being said, if/when I ever find someone that I trust enough to introduce to my son, she will need to be very understanding that my son only has one mom and while we didn’t work out as a married couple, she is a great mom and we still work together to make sure we’re on the same parenting page.

    I wish you luck in breaking the news to your ex – I hope it goes well.

  4. Andy — Your comments are greatly appreciated. And you’re right…the ex-wife only needs to know that I’m *dating*, no more no less. And since there aren’t any plans on moving to Florida (at least not any time soon…lol), then maybe downplaying it is probably the best suggestion.

    In terms of being on the rebound, I waited almost two years before taking the leap of faith that was this new relationship. I think my previous experience of trying to find love via a dating website in order to fill the void of loneliness and emptiness was probably the “rebound” in me. It’s when I stopped looking and starting trying to like myself again that K came into my life.

    KIm — Thanks. I’m glad I got a woman’s perspective on this. I, too, thought email or Facebook would be a sucky way to find out. And the sooner the better at this point really is the best way.

    Gary — Thanks for the well wishes. I really wish I had found some of the many single/separated/divorced parent websites in the months following my separation, as it would have really made 2007 and 2008 much easier years for me to handle, I think.

    Thankfully for me, K is already a mother of two and knows that my children are mine and her children are hers…I don’t think there are any misconceptions about either of us wanting to fill voids or trying to play another role of parent for somebody else. I’m just hoping that her kids end up liking me and see me as “Todd”, not dad…and I’m pretty sure K feels the same way.


    Awesome comments. I really appreciate the feedback.

  5. I think it’s natural that you still have some feelings for your ex. Not necessarily romantic, but you don’t want her to feel hurt. She’s the mother of your child, after all. And you two spent significant time and emotional energy together.

    That said, life moves on. That you are dating is great. You definitely should tell your ex about the new girlfriend before the new girlfriend meets your child. Just keep it focused on facts, not emotions. It’s a necessary step in moving on from the divorce of your marriage.

    It’s great you are so sensitive to all concerned.

  6. yah.. just dont make it a huge deal. you have been apart for 2 years. the next time you are talking to her (on the phone or otherwise) just say,, hey.. i wanted you to know im dating someone, as we promised to tell each other. if YOU make it a big deal it will BE a big deal. gawd dont go on about how much she is your soul mate 🙂 lol.. i know you wont,,but that made me laugh.

    her biggest concern will likely be the boy ( has lost me for a moment…OH “b”) so if this is mentioned reassure her you will not have ks involvement in your life mess with bs.

    we are all adults here.

    arent we? 🙂

    we may not be,, my ex sure isnt 😀

  7. Hey CBG,

    Your situation is eerily similar to my own. 🙂 We were separated for 2 years before divorcing. It’s been a year since the divorce was finalized, so 3 years since separation. I fell into a whirlwind romance at the end of November, and we’re blissfully happy together.

    I’m lucky in that my ex-wife started dating a few weeks before I did, coincidentally. She told me once it became serious. So I told her as soon as I had a girlfriend. I’ve met her boyfriend (recently escalated to fiance) a few times, and she met my girlfriend once, briefly.

    You should tell your ex. Just mention it casually, “Oh, by the way, I’m in a committed relationship with a wonderful lady who’ll be around our kids a lot. Just let me know if you want to know anything about her. Would you like to meet her soon?”

  8. > maybe downplaying it is probably the best suggestion.

    I wouldn’t suggest it – manipulating an ex-spouse is almost never a good idea. 🙂 It’s not really her business if you want to get married or move away or whatever. It certainly impacts her, but that doesn’t make it her business.

    You don’t need to advise her on how serious your relationships are, unless you get engaged or something, and at that point yeah you should tell her. But she ain’t your pal, she’s your ex. 🙂 Do continue to be nice, that’s wonderful! But don’t try to play her emotions or second-guess her reactions. Just tell her what she oughtta be told, be mindful of the impact of your choices on her (via your shared kid), and then be nice about it all.

    That’s my $.02. 🙂

  9. DadsHouse — I appreciate the kind words. I would like to think I’m the rule as opposed to the exception when it comes to dealing with ex-spouses…but I get the feeling I’m not.

    Jill — You’re absolutely right. No need to be all dramatic about the situation…just be straight forward and to the point.

    Scott — I think that’s where my guilt comes in…because I think I’m the first one to be dating since the marriage break-up. I think if she had found somebody first, I wouldn’t feel even remotely as awkward as I do. I appreciate your $.02. Thanks!

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