How do I talk to the woman my male best friend is dating?

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This is a follow-up to the thread I posted during my soul-shattering heartbreak at the beginning of this year after I found out my best friend (whom I had a very deep crush on) was dating a coworker 10 years his junior and 6 years younger than me: https://wrongplanet.net/forums/viewtopic.php?t=302612

So I'm almost fully recovered from that heartbreak (but not 100%). I'm accepting her as his ball-and-chain. If you've seen my other posts, I see dating as the first stage of a marriage and am having trouble understanding the concept of dating where marriage isn't the goal. My best friend seems to be more involved with this chick than other women I've seen him with, and he's talked about having kids with her. He's been engaged before, and his siblings are married with one kid each. He's probably almost ready to settle down. I'm pretty sure she WILL eventually make it to the altar with him on their wedding day, say "I do," and become his girl.

She's not a bad person, and she gets somewhat enthusiastic when I say talk to her in their store. I'm trying to be chummy with her in order to not look like a homewrecker and to keep his friendship. I even bought a pair of earrings from her new Etsy store to support my best friend's spouse. To know her better, I'll eventually befriend her on Facebook and invite her out to eat or drink 1 on 1 once I heal further and get used to her. I respect marriage and backed off from my crush, knowing that he'll become hers at their wedding. But I still have questions: WHY? What did they see in each other to invest their future?


When I talk to her, what should I ask her about what she thinks of him and why she wants to build her future with him? Should I say anything as if he was going to propose to her? Should I mention anything about marriage at this point? Or should I treat her like a single woman (which she still legally is)? Should I tell her how lucky she is to have/ be getting him?

What should I ask my best friend related to their potential eternity together?







I don't think badly of her. I hope she makes you happy. It's just a lot to ask to watch your future walking past me.- Dessa, "Call Off Your Ghost"

Hey, good for you being friendly to her. I've been there and wouldn't have gone to this much effect. You didn't need to go to all this effort, but you have, so that shows you are a caring person.

Don't ask her about her relationship with him. It's not any of your business. If she volunteers info, that's fine, but don't make her uncomfortable by prying. Also it will just hurt you.

Try and turn this into a more positive meet up. Forget about him, just get to know her.

It might be better to connect over things other than her boyfriend. Find something you have in common and talk about that.

Ask her things like, does she have any brothers or sisters? Does she have any pets? How is work going? Does she have any holidays planned this year? Has she seen anything good at the movies recently?

Just keep it friendly and casual.

So I got the earrings I ordered from her Etsy store today. She was really thankful that I was her first customer (! !) and chipped in an extra pouch and a sweet note thanking me. And, believe it or not, she wrote "Miss" before my name on the envelope (because thanks to her, I'm very likely staying a "Miss" unless I can find a relationship when I'm much older)!

My best friend shared her Facebook post with the link to her store, so that's how I found it.

And I managed to see her in their store yesterday and we had a nice conversation about jewelry. She has a much more sophisticated style than me.

However, nobody answered my question about what I should ask HIM about her. Anything?


Should I tell her she's lucky to be getting him?

Well at first I was going to say no, but if someone would actually tell me that the man I like is a good bloke and I'm lucky to have him that might be reassuring and I'd feel warm and fuzzy inside. I do like it when people say they like him and say good things about him.

You're not obligated to ask either of them about their relationship, so if it hurts too much to talk about it with them you don't have to. But if you do want to, try not to pry. Don't ask anything too personal. Maybe just tell them you're glad to see them happy together, but if that's a lie, you don't need to say it.

I would say....just steer away from the whole thing.

Sure, be friendly with her when met, but you are not obligated to become her friend - and you are not obligated to stay the guy's friend.

And trying to investigate why he chose her over you, would not do any good for you - and I doubt you will ever get a honest and clear answer from him (because he might not want to hurt you).

This is only gonna hurt you unless you get your own boyfriend.

I second what Boo said. If they do get married, you're friendship with him won't be the same.

But I can't cut him out of my life just because he's taking someone else as his lawfully-wedded lovergirl. Can't I befriend both of them?

Move on. Two's a party. Three's a crowd.

He chose her and I know it hurts but you need to leave them alone especially since YOU have romantic feelings for him.

I'm in the process of getting over that crush. I feel that getting to know her might finish the healing process.

And my best friend is friends with some of his other female friends' romantic partners. Why should I dump his friendship if he didn't dump his other female friends when they settled down?

I don't think so.

Yeah, you definitely still love him and I feel you're doing all you can to stay in his life and trying to figure out why he chose her.

Finally, you also seem to be trying way too hard to be nice and friendly to the new girlfriend.

You don't have to be friends with her.

Polite yes, but not friends.

Perhaps you do genuinely like her, but it seems more like you're using her as leverage for your 'healing process'.

My suggestion is not to stop being his friend, but instead of trying to get closer to them both and kind of intrude/third-wheel your way into their lives, maybe it's better you have some distance to get over him first.

It can definitely be easier to stay friends with a guy if you are also friends with his girlfriend. The thing is, if you start asking too many questions about their relationship, she might see you as a threat, or think you might become a nuisance to her. I know the situation sucks, whatever you do. Hang in there. Don't be afraid to put some distance between you and them, to let your feelings fade.