My (27M) GF (22F) is upset I haven’t proposed on our trip. How do I fix this?

Shirley Stafford Hours
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The sun dipped low over the California coast, casting a golden glow on the beachside restaurant where Jake, a 27-year-old with a knack for spontaneity, clinked glasses with his girlfriend, Lily. Their week-long Disneyland adventure, filled with rollercoasters and romantic dinners, felt like a fairy tale—until the final night. Lily’s eyes sparkled with hope, expecting a ring to seal their two-year love story. But Jake, caught off guard, had no proposal planned, leaving her heart sinking like a ship in a storm.

Back home, Lily’s disappointment spilled out. She’d mistaken Jake’s hints—talk of rings and baby reels—for a promise of forever. Jake, blindsided, dismissed her concerns with a breezy “relax,” igniting tension. Their story, shared on Reddit, captures a classic relationship hiccup: when love’s magic meets mismatched expectations, the path forward demands delicate steps.

‘My (27M) GF (22F) is upset I haven’t proposed on our trip. How do I fix this?’

My (27M) GF (22F) and I celebrated our two year anniversary in early February. We took a trip to Disneyland in CA, and had a nice week-long beach getaway. Great views, water activities, and romantic dinners.

On the last day of our trip, we had a nice romantic dinner at a restaurant on the beach about an hour or so away from where we were staying. I guess during that dinner, she was awaiting a proposal. Which I didn’t have for her.

We moved in with each other a year ago, and despite my worries of it being too soon, we get along great. We are both clean, respectful, and overall best friends. Money has just been tight. We live in a one bedroom. And don’t have lots of money to go out all the time.

I changed my timeline for her. But I guess I never had a timeline as I’d been single for so long before her. I never thought I’d want kids and stuff, but now that all changed as I grow more in love with her. But I don’t want kids right now.

I guess I’ve given her “mixed messages” as she puts it since I’ve hinted at those things. Like asking what shape ring she likes, sending baby reels, and we both get drunk and talk about babies. But I’ve explained to her that we can’t right now. I think she wants children soon though.

After we got back from the trip, she asked me why I didn’t propose. She was under the impression I would even though I never mentioned that. She told me that she’s shocked I didn’t, and thought we were on the same page.

Which we are. I 100% wanna marry her. But it will be a surprise, and I need money for the ring. She started talking about her timeline and I told her to just relax. Stop stressing. She’s so young. At 22 I didn’t want any of that.

Jake’s non-proposal at the beachside dinner reveals a disconnect common in young relationships. Lily, at 22, saw the romantic trip as the perfect moment for a ring, while Jake, 27, feels financially strained and unready for marriage. His casual hints about rings and babies fueled her hopes, but his dismissive “relax” when she voiced her timeline closed the door on meaningful dialogue.

This reflects a broader issue: communication gaps in relationships. A 2022 study by the Gottman Institute found that 67% of couples struggle with aligning on major life decisions like marriage. Jake’s mixed signals—dreamy talks without clear intent—left Lily feeling unheard.

Dr. Sue Johnson, a leading relationship therapist, emphasizes, “Love thrives on emotional responsiveness—listening and validating your partner’s needs”. Jake’s dismissal of Lily’s timeline eroded trust. He could rebuild it by openly discussing his financial concerns and co-creating a loose timeline, like saving for a ring within a year. Honest dialogue, rooted in respect, can align their paths.

Here’s the feedback from the Reddit community:

Reddit’s takes on Jake’s situation crackle with sharp insights and humor. Commenters dive into the mess of mixed signals, dissecting Jake’s dismissive attitude and the couple’s misaligned timelines.

Many call out his “relax” comment as patronizing, urging him to listen rather than shut Lily down. Others question his financial excuses, pointing to the costly Disney trip as evidence of skewed priorities. The community leans toward supporting Lily’s right to clarity, emphasizing that love requires open communication over vague promises.

carolynrose93 − 'money has been tight'. 'Weeklong trip to Disneyland' Pick one. You are for sure sending mixed signals. it's fine if you're getting ideas about what kind of rings she likes, but make it clear that it's for a question that will be coming LATER. You say you're best friends but you're on different pages and different timelines. Communicate with her.

barbaramillicent − Yeah… you are sending mixed messages. And you’re not “on the same page” or she wouldn’t be expecting a proposal when you aren’t ready to propose. I think you need to have more clear conversations about the timeline you’re comfortable with and get over this idea that a proposal needs to be a surprise.

You don’t have to get her an exact date, but she deserves SOMETHING. Is two years too fast, you’re thinking closer to year 3, 4, etc? You want to wait until your 30s?Do you have goals you want to reach personally or as a couple first? Etc. “Relax” and “stop stressing” is not communication. It’s just trying to shut her up.

It’s okay to want to slow down. You shouldn’t rush things like this. But come on. You can’t ask her about ring preferences and then be surprised that she thinks you’re ring shopping. Of course she’s gonna think that.

ThrowRADel − You should communicate your timeline instead of telling her that she should relax. Aside from how paternalistic and patronizing that is, her being able to plan out what is important to her and her life goals is more important than your insistence on a 'surprise' proposal.

It's a major life decision that has pragmatic implications and she will never feel safe or comfortable until you talk about timelines - she has brought up that conversation and it's really insulting that you refuse to discuss it, it absolutely will seem to her that you're stringing her along.

Is she too young in my opinion? Yes, at 22 she doesn't really know who she is as an independent adult. But she is still your partner and deserves your respect and to be able to make important life decisions as a full partner.

[Reddit User] − She started talking about her timeline and I told her to just relax. Stop stressing.. This part is the most concerning part of the story for me.. She discussed what she's looking for out of a relationship, and you shut her down.

If you want a good relationship that will last the rest of your life, you need to learn how to listen to other people instead of just telling them to 'stop stressing.' If my partner said that to me I would be gone. I'm serious. It's very common especially for men to talk down to women this way.

What you did was condescending, dismissive, disrespectful, and on some level, cruel. You treated her like she isn't allowed to have a voice and discuss things unless you approve of it. That's wrong and unhealthy.. You need to fix that asap before you cause her self-esteem issues for life.

It's completely okay for her to have a timeline, to have preferences. It's common for men to string women along for years and then never marry her... a timeline so that she isn't taken advantage of is completely fine and healthy and it only speaks to how you treat her that you don't want to her to have safety, assurance, and security

but instead just want her to have blind faith that you'll eventually propose and eventually want kids. Do I think she's rushing it a bit? Yes. But I also think she's an autonomous human being who is allowed to want things from her life. And I would never shut down my partner like you did.

I'm dead serious when I say you need to do some serious self reflection, because right now it looks like you only dated someone younger so you could control them and tell them what to say, what to do, how to act, etc.

If you aren't willing to listen when your partner lays out what they're looking for out of life, you need to break up entirely because you aren't mature enough to be in ANY relationship.

Ask yourself and answer truthfully. How often are you dismissing her feelings when she brings things up? How often are you compromising? How are often are you listening to her, thoughtfully, and participating in 'active listening' as opposed to just talking down to her like you did in your example?

Sneakys2 −  I guess I’ve given her “mixed messages” as she puts it since I’ve hinted at those things. Like asking what shape ring she likes, sending baby reels, and we both get drunk and talk about babies. But I’ve explained to her that we can’t right now. I think she wants children soon though.

It sounds like you have given her mixed messages. You’re asking about ring preferences but then pulling back and saying you’re not ready. It’s totally fine to not want to do get engage right now, but you need to clearly communicate what timeline you’re thinking.

What financial milestone are you waiting to hit? Do you want to move in with her? When do you see yourself wanting to get married? To have children? You’re making a lot of assumptions right now. You both need to have a real conversation where you both outline clear expectations of what your respective timelines look like and go from there. 

Dickduck21 − You cannot be on a week long Disney trip and also claim money is super tight. You clearly make happen what you want to happen financially, so it sounds disingenuous. Two years would be fast for an engagement but be honest. Communicate.

janabanana67 − At 22 I didn’t want any of that. Great for you, but at 22, she is thinking of marriage and kids. How can you be best friends and not understand that. If my BF told me to stop stressing and relax, I would have told him to pound sand.

Hex_Spirit_Booty − Money is tight but you can afford to go to Disneyland for a week lmao?

InsertCleverName652 − You are sending mixed messages, but you are not wrong in waiting to propose. Sit down and have an open conversation. 'I definitely want to marry you. I do not have money for a ring or wedding right now. Let's make some financial goals, a plan, and a budget so we can prepare for our lives together.'

Livid-Addendum707 − Money is not that tight if you went on a week long trip to Disney. I’m not gonna lie I’m hearing excuse excuse excuse, you live together already what’s the hold up?

The “I wanna marry you I promise” only works so long before it’s empty words. Sit down and discuss a timeline, if that timeline isn’t something you can commit to, then you might not be suitable for each other.

Jake and Lily’s Disneyland drama is a whirlwind of love and letdowns, showing how quickly mismatched expectations can derail a fairy-tale moment. Jake’s heart may be in the right place, but his dismissal of Lily’s hopes underscores the power of clear communication.

Have you navigated a moment where love clashed with differing dreams? Share your experiences below—how did you find common ground or move forward? Let’s keep the conversation rolling!

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