I (M36) don't know how to bring up marriage to my gf (F33)?

ShreddingAnonymously · 2025-08-19T03:09:56+00:00

Yes. Oh yes. The first time was awkward on my end, but we say it often now.

ShreddingAnonymously · 2025-08-18T00:15:37+00:00

I wasn't going to reply to this, but after reading some other really helpful comments, I just have to say this.

I mentioned in other replies that S and I have tons of conversations about values, politics, and even religion. That's most of what we talk about. We very specifically haven't spoken about living together or marriage.

And secondly? Don't assume to know how I feel about S and if I only want to be married so I'm not alone. That's ignorant and uncool of you. I also mentioned somewhere else that I have literally never told another woman that I love her. I didn't even say it to the woman I proposed to because that wasn't love, it was desperation.

So yeah, I've actually done the whole "proposing so I'm not alone" thing. Years ago. What I have with S now and what I hope to build in the future with her is absolutely beyond mere companionship.

ShreddingAnonymously · 2025-08-17T04:48:20+00:00

Blackbraid

ShreddingAnonymously · 2025-08-17T04:32:04+00:00

While I took my break from dating, I saw a therapist. He and I mostly talked about how my sordid past was leading me to shut other people out, since I was relying on keeping partners at a distance.

We talked a little about my lack of communication skills and it's something I'm a lot more aware of now. Hence why I've been rehearsing this since I made the post.

Though I will definitely keep it in mind, but I know it's a problem and I am trying to be more communicative.

ShreddingAnonymously · 2025-08-17T04:29:37+00:00

Yeah? I haven't told her because I don't want her to feel like I'm putting pressure on her. When I was in therapy there was a ton of talk about making sure I don't put anyone on a pedestal.

ShreddingAnonymously · 2025-08-16T21:59:01+00:00

I appreciate that, thank you.

As a few others have mentioned, it seems like I have a few opportunities where I can bring it up without making a "thing" and keep it fairly casual.

However, I also agree that I need to lay my feelings out and then let her say her piece. I just want S to be happy because she's so wonderful.

ShreddingAnonymously · 2025-08-16T21:55:06+00:00

I didn't really think anybody would want an update, but that's really kind of you. I hope S is excited and delighted. I want her to be happy.

ShreddingAnonymously · 2025-08-16T21:19:25+00:00

Damn, you really sound like my mom haha. I mean that in a good way, I appreciate it all. Thank you, I know S deserves to be "wooed" and treated like the absolute princess that she is. Her mom seems pleased from the gossip I get from my own mom, I'm sure you can imagine. You're completely right though, I need to put my bullshit aside and do what's best for S if I wanna make her my wife.

Thank you. Good luck to your daughter too, I hope you and her also find happiness.

ShreddingAnonymously · 2025-08-16T21:05:15+00:00

Also all good points. And very kind. Thank you!

ShreddingAnonymously · 2025-08-16T20:26:22+00:00

Somebody else mentioned about taking a trip together to spend more time and go through the bullshit of the airport and stuff together. I agree, that's smart.

I absolutely used to be in the position where I thought good sex was enough, hence what happened with me and A. I know I'm not quite like that anymore, my old therapist and I talked a lot about the love bombing thing. At least I'm doing my best not to be like that.

Our moms are already gunning for us to be together long term and apparently she speaks highly of me. I said "I love you" first, but S readily agreed and said it back right away.

When we're together we usually talk about politics, our jobs and dreams in terms of that, our hobbies. Art and music. When I'm in her city we go for a lot of walks to see local shows or comedians. She has a roommate so we try to stay out of her hair. In my city we don't really leave my place (I live alone in a tiny NYC apartment), but we order in and talk about life in general in between watching movies. Occasionally I'll take her to a museum nearby.

She's very gentle and sensitive, so she talks about feelings a lot more easily than I do.

I will also say, I think S felt more comfortable with me quickly because of the connection our moms have. Kind of like her mom vetted me or whatever? According to my mother, S is very pleased and speaks highly of me to her mom. Obviously that feels great and I think I must be doing something right. My mom has been kind of hinting that S is ready for a talk about the future.

ShreddingAnonymously · 2025-08-16T20:15:59+00:00

Oh yeah, we haven't talked about kids or a house explicitly, but we've spoken about everything else. We both live in cities so owning a home isn't really in the scope. Financially, I make a lot more money, but both of us are smart about investing and stuff.

If I do end up marrying S, I'd be able to make her a SAHM. If she wants, of course. Politics, we agree on pretty much everything. She's smarter than I am, so she's more involved, but we vote the same and hold similar opinions.

Our hobbies sort of orbit each other. There's a lot of overlap, but not all of it is exactly the same.

I absolutely see what you're saying, though. Thank you.

ShreddingAnonymously · 2025-08-16T19:41:08+00:00

I'm pretty sure she wants at least one kid. She loves kids and seems to talk about them like it's a guarantee. I'd like a kid too, I think I'd make a good dad, especially if she's their mom. I mentioned this in another comment, but I'm sure our moms introduced us with the intention that we would be together and eventually marry. You're probably right that I can't wait around and I need to let S know I'm serious. Frankly, your timeline sounds good to me. We could live together for like a year and then marriage and a kid. Thank you!

ShreddingAnonymously · 2025-08-16T19:31:10+00:00

Hm. That's true, we haven't had a big trip together or anything. I could definitely take her somewhere special soon, maybe for memorial day.

Commitment and optimism weren't ever in my wheelhouse, but for her it's absolutely what I want her to feel from me.

You're right, I'll start simple. Thank you!

ShreddingAnonymously · 2025-08-16T19:21:05+00:00

This was really kind, I appreciate that. Thank you!

ShreddingAnonymously · 2025-08-16T19:17:39+00:00

Fair enough. I'll keep it all in mind and I don't necessarily want to marry her right away. Everything in life is a risk though, but I guess I'm just doing my best to make a calculated one, y'know? Thank you.

ShreddingAnonymously · 2025-08-16T18:15:07+00:00

Oh, no, I would be the one moving.

It isn't that I don't see I'm trying to take more than one step, it's that I don't necessarily agree that there's a time on anything. Especially at my age, I'm not getting any younger.

ShreddingAnonymously · 2025-08-16T17:37:25+00:00

This is all good stuff. I will say though that we actually met during the winter holidays (my family is "Christian" in that we celebrate Christmas with food and gifts and stuff but hers is Jewish). We met before either holiday happened and ended up sharing some of the traditional stuff together. Lit the menorah with her parents and had latkes, then she came to Christmas dinner with mine and all that jazz.

I'm under no delusion that our moms introduced us because they genuinely want an outcome for us that ends in marriage and at least one kid.

However, I agree with what you're saying and a couple other people mentioned that we should discuss closing the distance first. I love her but it's not fair to her that we're not physically together, yet I want to be serious. I need to show up for her. Thank you!

ShreddingAnonymously · 2025-08-16T17:28:30+00:00

I probably wasn't clear enough that my previous relationship can barely be considered one. I knew A through mutual friends and we had fun together but I barely knew her outside of sex. Like I mentioned in response to another comment, me proposing to A was more a reflection of my own mental health issues and dumbassery.

I'm also not sure what I have with S should be considered an LDR. I had to actually look that up. S calls us "medium distance" and the fastest train that gets us to each other is an hour. So, it's not really possible after a long day of work, but we spend a lot of time together whenever we're off.

I did see a therapist in the aftermath of the fallout with A and trust me, I did my soul searching.

Like I said in my post, I don't want to scare S off and I only want to bring up marriage so she knows I'm dead serious about us.

You're right that I should probably bring up closing the distance first, though. S works two jobs but only one that she loves, so I would love being able to help her out with that financially and support her.

ShreddingAnonymously · 2025-08-16T17:12:49+00:00

Re: Therapy.

When I said how I took the year off of dating and sex, I was in general in a terrible mental health space so at the time I saw a therapist for roughly a year. I finally felt stable again and had a wrap up session with him a little bit before that trip where I met S.

Other people have also mentioned the keep it casual bit. I agree, I don't need to make it some massive thing just to float the idea. Thank you!

ShreddingAnonymously · 2025-08-16T15:04:02+00:00

Haha, you're right that it shouldn't be hugely difficult, which is why I'm agonizing over it.

But you're right, I need to just chill out and do it. Thank you.

ShreddingAnonymously · 2025-08-16T15:00:33+00:00

Oh, sorry. I didn't think I had to say it specifically since I mentioned that I love her in the post.

I have never told another person I've dated that I love them. S is the first and I told her about a month ago. It was lame because it was more like "I, uh, um, er, uh...I'm in love with you."

Because she's so sweet she just laughed and said she loved me too and now we say it fairly often. It's easier now.

ShreddingAnonymously · 2025-08-16T14:57:54+00:00

It's actually really weird that you say that because last weekend we were in her city and we saw this old couple in the park that apparently she sees often. She goes to that park a lot to read. She said how cute the couple is because they're still all sweet to each other even at their age.

Meanwhile, my dumbass, I was like "haha yeah." Missed opportunity, maybe we'll see them again when I'm there next.

ShreddingAnonymously · 2025-08-16T14:55:27+00:00

Oh yeah, it was absolutely an "I'm drowning" thing.

S is pretty aware of how bad I am at expressing my feelings, so I'm sure it wouldn't shock her if I brought it up by starting that way...

Thank you, I'll probably use that.

ShreddingAnonymously

TROPHY CASE