Dating Dilemma: When YOU Feel She’s Not the Right One for Him…

Written by on Tuesday, December 22nd, 2009 with 20 comments


Yesterday while I was in Hell, *ahem*, I mean Herald Square , a random guy approached me right after I had just finished a dentist appointment to fix a chipped back tooth. (It chipped the other night while I was eating mussels and had bitten on a tiny rock – WTF, clean your mussels properly, resty’sfor shiz!).
Anywho, he comes up to me and asks:

HE: “I know this sounds crazy, but can you give me just 60 seconds of your time?”
ME: “Ahh, for

HE: “I just need some advice about something I’m about to do…”

I have no idea if this dude came up to me just bc he wanted talk to me or if he genuinely needed another person’s perspective. I decided to believe the latter…

ME: “OK, what is it?”
HE: “My best friend is going to ask his girlfriend to marry him. Today. They’ve been dating for a long time.”

He pauses for a sec and says

“Thing is, I KNOW he shouldn’t marry her.”

ME: “Well, why not?”
HE: “She’s not a good person. She’s a liar
and is mean to him and just an overall terrible person. What should I tell him?”
ME: “Don’t tell him anything.”

I’m almost positive this guy has given his opinion about his friends gf to him in the past (it’s too hard not to), but doing so right before his friend is about to propose? IMO, that’s just not a good idea…

HE: “Even if I know she’s not right for him???”
ME: “Yea, bc it’s his relationship and he has to make the decision on whether or not he wants to be with her.”

HE: “But, I’m his best friend. If I know it’s not the right thing to do, shouldn’t I help him out?”

ME: “I know how you feel. But if he hasn’t realized – after being with her all this time – that she’s not a good person, you telling him that she isn’t probably won’t change his mind. And he just might get mad at you for making his ‘special’ day, not so special for him.”

“Besides, he’s an adult. He has to decide if she is the right one for him.”

I started to walk away after telling him this bc, since I had just come from the dentist, half my face was still numb & immobile. If you could see the look on this guy’s face while I was talking to him with just half my face moving – it was PRICELESS, LOL!

In any case, I could tell he was still confused as I walked away… and I kinda felt bad for him bc it’s a tough thing to see your friend potentially make a huge mistake.

So…would you tell your friend your true feelings regarding their current partner/potential spouse?


p.s. – Don’t forget to enter my Undercover Starlet giveaway – to win a dress or a journal!! Enter HERE

20 Comments on “Dating Dilemma: When YOU Feel She’s Not the Right One for Him…”

  1. Even though it's their decisions, if I really felt one friend shouldn't marry the other, I would have to tell them why, even if I was un-invited to the wedding afterwards.


  2. That's a hard one…then it comes off like you like the guy even when you're just trying to look out for him…booo!

    Come enter my giveaway!

    Miss you!!

  3. My roommate had been dating a guy that was terrible. He lied about having kids and about where he graduated from. Our little circle had proof and we told her but all she did was get mad so we let it go. Well she found out he'd lied about having other children and finally woke up and dumped him. So basically she had to make the decision not us.

  4. Weird that this guy just come up to you out of nowhere to ask such a personal question haha.

    As far as what I would do…unless my friends' s/o was causing severe harm to them or the relationship and I had concrete evidence to back it up, I wouldn't say anything. It only becomes my business if my friend is clearly miserable.

  5. Ooh, that's tough… completely understandable to want to look out for your bestie… BUT, unless your bestie asks for your honest opinion, it is your job as his/her bestie to support them, even in their relationship decisions. (There are exceptions, of course, such as extreme, bad situations, like abuse or something… then the rules change completely!)

    Hope your tooth feels better!
    xoxo J

  6. First, I just have to say that I absolutely adore the fact that this stranger walked up to you with this ish instead of seeking out maybe a female friend – gotta love New York!!

    Second, I would keep out. I have walked the line of being the BFF who critiqued someone's BF/GF, and, as much as I felt that I was trying to HELP the situation, it only left the friendships in tatters. It's always essential to look out for friends when it comes to relationships; but love is blind. Sometimes people have to wake up on their own!!

    Thank you, thank you, thank you for the birthday wishes, Amy!! They totally made my day!! And I just have to say…I literally cannot make it through the day without my daily dose of Midtown Girl – love it far too much; I wish I had found you sooner!! 🙂

  7. I think you are dead on, that if this guy has been dating this girl for a while, that his friend has shared his thoughts on the matter with him, and still, this guy is proceeding with the relationship. So, you are absolutely right; best friend shouldn't ruin this guy's day telling him something he's already heard and didn't believe.

  8. absolutely not…i have been in this position and all you can do is listen and help clean it up when it goes south! they will turn against you…love makes people crazy!

  9. Good advice- ultimately, it is HIS decision, not his friends- no matter what he friend does/says… tough situation though!

    Hope your tooth feels better!

    PS: your My Stocking will post tomorrow @ 10am 🙂

  10. If I had concerns about my friends girl, I might tell him to be careful in the early going, but to tell someone that his girl is no good right before they are about to get married? Nope.

    Hope your mouth feels better!
    Geez, who needs Dr. Phil when MG is around!? :))

  11. I think it depends on a couple of things. If it was my BFF and I *knew* she was marrying a bad guy, not just a guy who's personality conflicted with mine but a guy who was bad for her, I'd probably say something- if she asked.

    Honestly though, don't we ladies ask our friends opinions about this stuff long before it gets to the marriage part? I do. I'm all about the "what'd you think???"

    For the record, several years ago a good friend's boyfriend made a serious pass at me. It was bad. (Turns out- I wasn't the only one, either!) I secretly hoped she wouldn't marry him but I didn't tell her until they broke up- 4 years later. She was furious with me for zipping my lip. I didn't want to hurt her and I did anyway. 🙁

  12. Things like that are such a double edged sword. It may be hard to keep your thoughts to yourself, but we need to keep in mind that (hopefully) we are all adults, and can manage our love lives accordingly.

    But don't our friends' opinions of our other halves matter? I know it does to me, and I always ask for opinions. I'm not one to rain on someone's love parade unsolicited.

  13. That is such a touchy subject. If my friend really wanted to know my opinion I would tell her in the most gentle way possible. EEEK. I don't ever wanna be in that position!

  14. I would tell her once and then keep my mouth shut…and then be there for her when it falls apart but never say I TOLD YOU SO. lol

  15. thanks bby !
    wow u r so lucky,u have something interesting so random happen to u
    if i were him,like u said,he was his BEST friend and the girl is TERRIBLE,its MARRIAGE we are talking about,im gonna risk my friendship,if he listen to me and still wanna be freidn,thats great,if he get mad at me and leave me,thats the risk.well as his bestfriend of course i dont want him to make such HUGE mistake,so i'll take the risk

  16. You do fell!it is a pleasure to know you:)

    Today, I preparing for Christmas, even we go Chrismas my husband parents in
    the home.We dears mothers fighting almost go either way, but rotate them.
    My parents and sisters live in Nokia.
    Sometimes i have got miss they much,but
    now my home is there and i`m happy.

    ♥Merry Chrismas♥

  17. Oh my, what a position to be in, I guess I'd speak up in the earlier stages of their relationship if I came across some negative info' about the guy, but the topic would never be raised again.

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