So I have been chatting with a woman who is 34 and from her profile and our chats, her ideal timeline is 6 months to get engaged (fine with me as I am \~40) and she can relocate.

We have talked for about 3 weeks and talked on the phone twice (scheduling 3rd this week). On paper and our discussions, our ideals align – kids, timeline, closing the gap etc. and she did emphasize that she wants to “capture big points and deal with small stuff later”. She mentioned she doesn’t want to be stay home mom and at the earliest, she would stay where she is until spring due to job stuff. I told her if we are “engaged” by that time it would be fine and also said if she comes to where I am she can take her time to look for an ideal job for her – no pressure from me.

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I did mention that I am switching job in late september so that month might be most ideal for us to meet since I would have 0 pto once i go on to the new job. She didn’t say no.

Should I try to press her to meet up and for those who are going/gone through this, whats the timeline like and any pitfalls or tips?

My current “ideal situation” is have her come for a week, I will pay for her flight/lodging. Spend time with her for a week and try to advance with her to some level to confirm some level of relationship. If she leaves and there’s not even kiss then I would see it as failure.

22 comments
  1. This is so unorthodox and weird that it’s hard to give advice. Overall it seems like a red flag that anyone is talking about engagement and children before even meeting. It’s like you’re online roleplaying a relationship. Or treating it like an arranged marriage. So it’s hard to tell what you should do in this situation.

  2. Pitfalls?

    You’re engaging in one right now: trying to solve for a future without ever having met.

    Even though you can absolutely nail quite a few things up front without meeting, sexual compatibility has no conversation analog that I’m aware of (though you can obviously talk in somewhat specific manners on things you like/dislike).

    And the only way you can solve for that is to make a plan to meet, make sure things work out, and THEN plan.

    I mean I could dig further, but that’s the most straightforward part, I feel.

  3. You’re treating this as though you are interviewing a student for a summer position at your workplace.

    Marriage is for life.

    Life.

    You need to spend significant time together, figure out how you handle conflict, expectations of one another at home, etc. before you can even begin to think about getting married.

    You guys want to be married. I understand. But don’t rush the process. Because divorce is horrible, as is living trapped in a very unhappy marriage.

  4. This is so weird. Not only doesn’t she care about you, you don’t care about her either. This reads like 2 lawyers discussing a relationship contract.

    If you want any advice it’s to stop talking about the future and just meet this person. Either in a videochat or a date

  5. My advice? Don’t plan out an engagement before meeting someone.
    My secondary advice? Don’t agree to get engaged with someone who doesn’t even live in the same city as you.
    My tertiary advice? Don’t get into a LTR at all.
    I’d put this woman on the back burner, so to speak, date locally, then if she comes to visit in Sept, see how things go.

  6. You know, I kinda made a face reading the first paragraph of this post, but then I checked myself and remembered that stranger things have happened in real life. You two sound like adults who know what you want and you’re both actively outlining what you want and negotiating the terms.

    On some level, a relationship *is* also a business deal, what with combining finances and intertwining lives together and having children together. Would *I* approach dating the way you and your lady are? Probably not. But just because I wouldn’t do something doesn’t mean it’s not going to work out for someone else.

    Some couples are better business partners than life partners, and vice versa. Maybe you and your lady can be both 🤷🏻‍♀️ who’s to say. If you’re ok with the terms being laid out and she’s on the same page as you, follow your instincts.

    Please update us in 6 months tho lol. I’m very curious if you’re actually engaged by then or if something else happens!

  7. Chatting online isnt real life. Meet asap. Be skeptical. Be open. Go from there

  8. you should apply for 90 day fiancé if this is your trajectory bc at least then you’ll get paid to ruin your life

  9. The cart is so far before the horse that it can only be seen with the James Webb Telescope.

    ETA: I don’t say that because you’re discussing your timelines for getting engaged. But she’s not even clear if she’s willing to meet in person?

  10. I would expect her to pay half for the visit. Or you both meet half way.
    That just screams, hurry up for alimony to me. 6 months is too short. But I’m a skeptical person. Prenuptial agreement if you do go through with it.

  11. This is the example I give when I ask people what they are looking for on the apps, I say I need to know so I can run and hide.

  12. Meet ASAP. Before even talking marriage, I would say you would need to spend several weeks together to make sure there is no hidden surprises. (Don’t need to be all in person).

    Meeting friends/family also helps.

    Otherwise, it is a big roll of a dice with odds stacked against you.

  13. You’re putting the cart before the horse. This sounds like an arranged marriage – which works in Asian cultures because divorce is SO discouraged, so you make it work no matter what. Coming from an Asian culture, I can tell you that you have to be willing to live with the consequences of potentially living like roommates if this doesn’t work – or we’ll see you back here in a year figuring out divorce documents.
    Meet the woman before putting kids and timelines on the table. Have a conversation face to face… go on a date that requires you both to be challenged… see if there’s chemistry (hold hands, have a first kiss, see if you both know how to give reassurance and compliments and thoughtful gestures to each other, talk about your struggles together, etc). Are you okay if she’s rude or a complainer or puts you down for your appearance or the way you walk or whatever?
    Also “If she leaves and there’s not even kiss then I would see it as failure.” this is concerning. A relationship is not a test you can ace. Sometimes 2 people just don’t work and that’s no one’s fault. We all have different dna – physically, mentally, emotionally, spiritually, etc.

    A short courtship isn’t unheard of.. it happens everyday. Take it day by day, communicate, be very open with each other, consider premarital counseling. I would just encourage cautious optimism before jumping in head first.

  14. I looked at your post and comment history and there is one about a girls mother essentially interviewing you before connecting you with the girl.

    You probably should have led with that whatever cultural norms you have, what you’re doing may be The norm and that your criteria for marriage are likely far different than 99% of people on this sub.

    And that’s ok if it’s acceptable to you and the woman. Just would have saved you a lot of grief not to post this like it’s a normal arrangement.

  15. I’m not sure how I feel about this honestly. It feels like you’re paying for her companionship a bit since you’re expecting some sort of experience when you two meet. There’s zero way of knowing if she would even feel comfortable kissing or more on the first trip since this would be the first time you guys even meet.

  16. Meet immediately. There are countless people I thought I’d have chemistry with in real life… but didn’t. I wouldn’t really discuss anything further until you get face-to-face with each other. You’re creating false intimacy with all these really advanced relationship discussions right now and I would slow waaaay down. Getting engaged in 6 months is a red flag. Only husband hunters put those timelines on relationships that aren’t even real yet. Also it can take up to 18 months for the rose colored glasses to come off, so I would never marry someone before then.

    Also, her trip should be 50/50. If she’s serious about wanting to meet you she should happily pay half. You could just be getting scammed. There’s nothing preventing her from visiting you, not even really interacting with you, and enjoying her free vacation. Proceed with extreme caution and for the love of god don’t give her any money and don’t let her string you along with excuse after excuse about why she can’t visit.

  17. Dude this sounds crazy, slow down and get to know her before thinking about any of these things, what’s the rush?

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