We’ve known each other since college, both in our mid to late thirties. She returned home since graduation, while I’ve stayed put. She’s self-employed, while I’ve had the same 9-5 for over a decade.

We started talking again in late March and have been nearly inseparable despite living in different time zones. One doesn’t talk multiple times a day for hours on end, if we weren’t close friends. She’s recently started calling me her “best friend.”

Early on, she mentioned she was unsure if she’d ever get married or have kids. In recent conversations she’s told how many kids she wants, what names she chose. Then casually asked if I’d “impregnate” her.

Multiple times recently she’s asked if I’d marry her. Each time I was taken back, she asked like she wanted to grab dinner. If things lined up, I would.

What is she getting at? Why play the disinterested card then flip?

9 comments
  1. Do you want kids? If you do, I’d say go for it. I was in my mid to late 30s when I had mine and I wish I’d had him sooner, the longer you wait the less time you’ll have with your kids.

  2. Sounds like she is dropping you hints without making the first move.

    You can always learn to love someone, but for a marriage to really work, you have to like each other from the beginning.

    Me? I say fuck it. Ask her out on a date.

  3. No, never. So much easier to lose a wife or husband than it is a best friend, there are things that a spouse can do to you that are impossible for a best friend to do – cheating comes to mind, than there are finances sure you could lose a best friend for monetary reasons, but you’re practically guaranteed to have your finances entangled with a wife and with a best friend that’s not the case. I’ve had the same best friends for over 30 years, sure we’ve fought, but nothing that we weren’t able to get past. I was married once – lasted a decade, there were things that just couldn’t be mended – due in large part to the romantic emotions that tied us together. And frankly, I was really fond of her, like I got along with her on every level, She was my best friend (though not before we married) but the circumstances that led to our divorce ruined not only the marriage, but the friendship as well. If this person really is someone you consider a best friend – and not just someone you feel especially close to – than I’d urge you to caution and really reflect on the situation.

    Because you risk losing a best friend.

  4. You’d be so much better off to go on 50+ first dates.

    The chances that your best partner is someone you’ve known the whole time is zero.

    And if you’re not married and she isn’t married, neither of you is wanting a relationship anyway. Don’t do it because of flirting or babies.

    If it was going to be a good idea, you’d have tried it at 19.

  5. If you’re into her then say “I would love to go out to dinner with you.”

    She probably thought you didn’t want to be married or kids, and now she testing you to see what you say.

    She likely wants you to make a move

  6. I’m going to be straight with you… you’re not best friends. You’ve been courting each other with these long daily talks. This is pretty great because I bet you’ve talked a lot about your values and goals without front loading the physical bond. If you feel like you match on those important things, why not give dating a shot?

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