I need your advice about a man and his exes

by singlemomseeking on February 23, 2009


I recently went on a few dates with a guy whom I’d met at a party I’d attended with Depot Dad.

Everything about him looked good on paper: he’s my age, cute, professional, responsible, no kids, a dog owner, legally divorced. He came with good credentials — it turns out that he’s a friend of a friend — and he’s a good communicator (at least by texting).

Although the chemistry wasn’t instant, our conversations were easy and open. (I will add, however, that he’s very serious — I’m not sure if he gets my dry sense of humor.)

So, here’s my question:

This guy just bought a home, which he has been renovating like crazy. He called to let me know that he’s having a little going away dinner party at his condo before he officially moves out.

I was touched that he’d invited me, and I started to put in calls to find childcare.

But a few days later, he left a message saying that he’d like to chat with me about the party.

I called him back, and he explained that he wanted me to know who would be coming to the party. Yes, I’m listening.

As a preface, he explained that he once invited a date to a party, and his ex-wife was there, too. He went onto to say that his date hadn’t been too pleased about spontaneously meeting his ex-wife.

Anyway, he told me that this will be a small, intimate dinner party of eight, with the following guests:

1. His ex-wife (they got divorced two years ago, and have remained close friends)

2. Two women whom he briefly dated in the past year

3. A couple of neighbors

4. A couple of guy friends

5. And me

“Fun!” I said, flippantly. “Your exes and I can all sit around telling stories about you!”

He didn’t laugh.

Honestly, I have no issue with a man who remains friends with his exes.

As long as his boundaries are clear, remaining friends with one’s exes can be gratifying. (Feel free to tell me that I’m talking out of my tush and making excuses — because I’ve remained friends with some exes.)

Anyway, you can do the math: half of the women at this party have been intimately connected to him at some point.

To be honest, I’m not feeling too pumped about going to the party anymore. I don’t know him very well, and it might be awkward surrounded by all these exes.

Please be honest with me:

Am I being immature? Am I overreacting, as I’m known to do?

Should I just suck it up and go?


In the meantime, over at Singlemommyhood, we question how you know when you’re emotionally ready to date?

Read all about it here.

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{ 33 comments… read them below or add one }

casualencounters.com/blog February 24, 2009 at 1:40 pm

Alcohol is the solution to all such awkward social situations.

A few sea breezes and you and his ex-bedroom-buddies will be high-fiving it up whilst making risque jokes about his humorless cat-hating ways. Guaranteed.

casualencounters.com/blog´s last blog post…Casual Encounters Web TV Show, Episode 2


Apples February 24, 2009 at 12:59 pm

“Hey just bring a few of your exes along to even the odds.”



QTMama February 24, 2009 at 12:12 pm

Cats. We need to get some cats. Bring your cats.


QTMama´s last blog post…Cleaning House and I’m The Cat Lady


Jim Everson (Depot Dad) February 24, 2009 at 10:49 am

Hey just bring a few of your exes along to even the odds.

Jim Everson (Depot Dad)´s last blog post…Supernanny to the Rescue…or something


Hanna February 24, 2009 at 10:45 am

He he how can you resist starring in your own episode of “Sex and the City”?

I would be more uncomfortable if I were the ex, actually. Well maybe not. To me it kind of seems like a “I am king, look at the harem of women I’ve dated.” Unless he really is a cool guy who women still just want to be friends with.

The possibilities are endless.

Hanna´s last blog post…Email poem


Andrea February 24, 2009 at 9:55 am

Ok, I think if you are not feeling comfortable about going to the party, then this guy is not dating material for you. If you are not ok with one dinner party with his exes, think of a whole relationship with him having contact with them. That will not be comfortable for you.


Yummy Mammy February 24, 2009 at 9:45 am

No, would not like that at all. I personally would find it very uncomfortable and would probably be very paranoid about what the exes thought of me.

I once went out with a guy who had exes on speed dial. I often wondered if it was him hanging around them just in case they ever wanted him back or if they where just friends. But it would get annoying when I wanted some “me” time with him and 4 exes would ring up for a chat.

I go with the general rule that exes are exes for a reason and in the exes deleted bin they should remain

Yummy Mammy´s last blog post…The Four Man Plan


singlemomseeking February 24, 2009 at 10:23 am

Yes, Yummy Mummy, I am feeling a bit uncomfortable. But I’m not sure if it’s the exes, or the fact that he looks strangely at me whenever I say something flippant… Still trying to see if childcare will work out anyway.


Aunt Marge February 24, 2009 at 8:47 am

Hi Rachel,
I am adding my endorsement of all those that say “go the the dinner party”. Don’t think of the women, think of the opportunity to meet two new men and get to know more about the “host” by meeting his friends. The only “red flag” that I see with the “host” is that he may not share your sense of humor, which is really foremost in a successful relationship. So go – looking gorgeous – you gain nothing by staying at home – we regret what we don’t do, not what we do do.
Lots of Love,


singlemomseeking February 24, 2009 at 10:30 am

Yes, folks, this is a real live family member… “our Marge.” Usually Marge emails me on the side, privately… thanks Marge! I listen very carefully to all of her advice because she has the most loving, kind, giving marriage to one gem of a husband.


LeAnna in MN February 24, 2009 at 8:44 am

I haven’t read what everyone has said, but I’d say go for it, with a phone reminder to hit about 40 minutes in. Either set an alarm with your ringtone, or have phonemyphone.com call you at that time, or whatever. That way, if you need to “rescue the sitter” or something, you have that option if things are just going awkwardly. I’d take any chance I could to meet exes not for comparison’s sake but for the sake of hearing another perspective, seeing how he is in groups, etc.


Kari February 24, 2009 at 8:08 am

“As long as his boundaries are clear, remaining friends with one’s exes can be gratifying. (Feel free to tell me that I’m talking out of my tush and making excuses — because I’ve remained friends with some exes.)” EXACTLY how I feel and I’m friends with plenty of exes.

are you being immature, nope this isn’t a date later on it is like the first date right? That is stupid to invite you to it as a date and expect it to involve. exes. I say NOPE. You are not over reacting and you shouldn’t go unless you feel comfortable, explain to him if you’d have felt comfortable later on down the road but just not right away if you want.

Kari´s last blog post…This might just be a dating blog like I intended


T February 24, 2009 at 7:59 am

Hey, I’m friends with all of my exes so I can’t chide you or him for that.

Going to the party might be fun especially if you’re not feeling much chemistry. Just think of it as an opportunity to make some new friends.

Unless you really have already decided that you don’t want this guy in your life… in which case, I’d politely decline.

Its all you girl!!

T´s last blog post…Sometimes we just need to vent


Eathan February 24, 2009 at 7:54 am

It seems as if the ex to guest ration is a bit high. Even as a guy.. it gives me alarms. But it could be a good way to get some insight on what you can expect for the future, if you go forward with him.

Eathan´s last blog post…Question From A 15yr Old Reader


Susan February 24, 2009 at 7:42 am

I don’t disagree with any of the comments above – on the one hand, it might be an interesting evening…and certainly blog-worthy for us! 🙂

On the other, I think the fact you are asking us these questions indicates you’d really rather not go. (Ok, I guess you actually said that in not so many words.) I can’t blame you.

If your gut is telling you, “mmm…not this time,” I would tell him you really appreciate the offer and the fact he told you about the guest list up front, but that you’d prefer to do something special with him when he’s all moved into his new place. (especially so, since you have to find a sitter for M – don’t waste that on a night out you are dreading!)I would hope he’d appreciate and respect your honesty. If he doesn’t, well, that says something, too!

Susan´s last blog post…Knowing, learning, laughing


MindyMom February 24, 2009 at 7:41 am

How unusual! I wonder if he gets some weird satisfaction having his exes and his current date all in the same room? It’s strange that with such a small guest list so many represent women he’s been involved with. John F may be right about the fantasy!

I would go ahead and go. Have fun and see what you learn about this guy. If nothing else it will show how strong and confident you are.

MindyMom´s last blog post…Single Mom Posting & Playing Hooky


John F February 24, 2009 at 7:28 am

Oh hell—go! People are “exes” for a reason and the fact that he remains friendly with them certainly speaks to his integrity doesn’t it? I mean it could be an intimate dinner for you and him where he does nothing but talk about that bitch (or worse) he used to date!

The guy was courteous and gave you the heads up. He may be showing you off (after the pajama deal on TV you really can’t blame the dude) and that may be fine as well.

If nothing else, we are in a horrible economy and hey–it’s a free meal.

Just ask if you can bring a BIG bottle of wine, and if things get out of control and his fantasy of a sapphic orgy of all his exes materializes, please share the video!

John F´s last blog post…Sometimes You Just HAVE To Laugh


singlemomseeking February 24, 2009 at 10:42 am

Oh my John, you really crack me up!!

Free meal, fantasy orgy…. stop!


won February 24, 2009 at 7:26 am

When in doubt, don’t.

That is my personal mantra when trying to decide things of this nature.

Looking ahead, I do not imagine regrets over you not having gone. I imagine there is a greater likelihood of having regrets if you did go (if regrets were likely at all).

won´s last blog post…Pissed


wandamd February 24, 2009 at 7:15 am

PS: I agree with SingleParentDad, this probably won’t be your only opportunity should you guys continue towards a serious relationship. Maybe down the road it won’t seem like a big deal?


wandamd February 24, 2009 at 7:12 am

Well, I am good friends with my daughter’s daddy and I have a serious boyfriend. They have met briefly but i’ve not felt any need to force either into each other’s face. I think once you do that there is potential for either one to form opinions you might not be ready for them to have (like your ex weighing in on weather or not your current boyfriend is good for you).

While my current beau is very supportive of my friendship with my ex none of us feel a need to “hang out”.

I don’t know if in your situation I would worry about feeling akward that one night, but more that you need to determin what your level of comfort is in needing to meet these friends of his and ask him to respect that boundary.

Unfortunately because he’s serious, you might have to speak serious to get this point across.


Legal Editor Mom February 24, 2009 at 6:36 am

First, I have to say that I see nothing wrong with him or you remaining friends with exes. I am on good terms with ALL of my exes, and even friends to this day with two. I’ve never, however, invited them all over at once, so this does seem a bit odd. Still, he invited you to the gathering and was honest and considerate enough to discuss the situation with you first, which in my eyes, scores him at least a few points.

I’d go, looking your best and being as charming as ever, and see what happens. If nothing else, you’ll learn more about him, and get a better idea if this guy is relationship potential or not. And, just as important, you’ll see how he treats you and acts towards you in such an awkward setting. Go for it! But relax, so that you can have a good time in the process. It is a kid-free night out, after all. 😉


Wondermom February 24, 2009 at 6:28 am

I just have to say I love you, Rachel! You can’t make this stuff up! 🙂

As for the party, it could turn out to be a lot of fun and if not, it will definitely make for an interesting blog post! I agree with whoever said to make sure you have an escape plan. Maybe arrange for your sitter to call you after an hour so that if it’s just too weird, you can say M needs you and run away.

Crazy Computer Dad, I don’t necessarily think it’s a male/female thing…I think it’s more a me/you thing. I too have been involved with guys who were friends with exes but got jealous about me being friends with mine. I’d like to say I’m above that but I do have to remind myself sometimes about trust. I think it’s natural.

Good luck Rachel!

Wondermom´s last blog post…Small victory!


Dr.Leah www.singlemommyhood.com February 24, 2009 at 6:27 am

Speaking of clutter…can this guy just not let go?

Of course, go to the party just for the life experience. I’m thinking that there are financial connections between him and his “formers”, too? How pumped can they be to meet you? The whole situation has rather a “Big Love” quality.

Frankly, I’m intrigued.

Dr.Leah http://www.singlemommyhood.com´s last blog post…Beware of the “marriage museum”


Amy Sue Nathan February 24, 2009 at 6:24 am

It’s an odd situation and actually reminds me of a Sex and the City episode where Miranda is put in a similar situation, and the people at the table are really there to check her out and ask specific questions. I’m not saying that’s the deal here, but it’s equally awkward isn’t it? I think it would be classy and understandable to decline the invitation — but it wouldn’t be wrong to accept either. There is no reason for you to meet this man’s multitude of exes unless you’re going to have a long-term serious relationship. And, so many exes he stays friends with? On the surface that sounds nice – aww – great guy. Deep down, frankly, that’s weird.

Your book review will “go live” on my site tomorrow.

Amy Sue Nathan´s last blog post…‘Restaurant Week’ and coupon codes are great ways to indulge for less


SingleParentDad February 24, 2009 at 6:20 am

You’re not really selling this guy you know. Doesn’t get your dry sense of humour? What’s all that about?

I think we are all adults, and new relationships always have some awkwardness, but this does look like being a lot. I mean out of the six other guests (not including you two) he has married one and dated two others, thus a 50% ‘hit’ rate. Mind if they are still friends, this is likely to happen again, so if you don’t feel ready now, you will have other opportunities in the future.

SingleParentDad´s last blog post…Phantom Toddlers


Nancy February 24, 2009 at 5:23 am

If you want to continue dating him, why not take the opportunity to meet all the ex’s at once, lol

If you’re in limbo on where this guy could go as far as a relationship, go anyway, we can never make too many friends … networking.

I met a good g’friends through an ex of both of us. We’re still friends…. him, lol, neither have talked to him in years.

Just go, have fun, be the “new girl” everyone is checking out.

Your confident and can pull it off. He’ll be glad to see you don’t have a green streak and can hold your own in a possible pool of sharks.

Nancy´s last blog post…I could get used to this life …


Crazy Computer Dad February 24, 2009 at 5:02 am

It IS an opportunity to get out and have some adult time. It could be that the group are all close friends. If you are dating then wouldn’t you want to learn as much about him as you could? Seeing him around friends in a setting like that is a great way to see how he handles himself. You could see qualities that could help you make up your mind one way or another. If it is totally awkward and you are the only one that doesn’t fit in then maybe that is a sign?

Maybe setup an escape excuse? have an alternate plan so that if things totally go south then you can still meet up with some other friends and have some fun?

I find I meet a lot of women that REALLY want to hang on to their exes…but make it very clear they don’t want me to hang on to or around mine. I wonder why that is?

Crazy Computer Dad´s last blog post…….and the 80’s


Anita February 24, 2009 at 5:00 am

lol, Apples too funny!!

Nope couldn’t and wouldn’t and shouldn’t be expected to.


Allison February 24, 2009 at 4:34 am

Although, of course, if you do go, I would love to read about it!


Allison February 24, 2009 at 4:34 am

So, no women friends he hasn’t dated? That’s kind of odd. and what a small group. Hmm. I wouldn’t want to go either.


Apples February 24, 2009 at 12:53 am

I’d tell him I will pass because I can only handle meeting ONE ex at a time… HAHA… Seriously, I’d say that though. 😛


judy February 24, 2009 at 12:01 am

I’d be instantly jealous and feel icky about going ..skeptical and rather sarcastic …..however except for the ex-wife you do not know about the intimacy of the other relationships and are they set-ups for the guy friends??

Only go if you feel ok about going but I would verve away from asking him too many questions in advance. Appreciate his upfront honesty and if you decide not to go be just as honest…..keep it simple


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