Should I propose to my boyfriend?

[Anonymous]

We talked a lot about what we want the other night. He asked if I want to marry him and I said yes. When I asked him if he wants to marry me he said maybe (more like mayyyybeee). He then asked if that was me asking. I said no. He said good bc he wants a better proposal. I said that the guy usually proposes. He said women can too.

Our anniversary is soon. Should I propose? If so how should I go about this?

[Anonymous]

How long have you two been dating? Make sure he’s completely on board with marriage, his “maybe” might have been in a flirty-yes tone, but make sure you sit down and have a serious serious talk about it.
Choose a meaningful location, like a first hiking spot you two ever went to together.
Rings of course, has he discussed what type of rings he likes? Also, buy both of your rings. One for you, One for him. Or a matching pendant or bracelet to be more modern 😝
Get down on one knee if you feel comfortable, or you could just stand together and pull it out of a pocket and pop the question.

[Asker]

Definitely was in a flirty tone. He hinted at having a ring but then all but told me to propose. We've been together almost 3 years. He proposed to an ex but she turned him down. We had the talk about it - expectations, moving in together, what we want.

We have been seeing each other a lot more and he's been a lot sweeter. I kind of want to do this but im also worried aboutbthe chance he could say no.

[Opinion Owner]

I’d say go for it! I just needed a bit more context behind it. However, since you mentioned that he proposed to an ex but she said no, I think he is a bit hesitant of proposing to you because he still has that rejection in the back of his head… But that doesn’t mean he doesn’t want to marry you!! I’m sure are worried about rejection too.. Proposal is hard, I still suggest talking to him more, more about “If I did propose, would you say yes?” and see what he says.

[Asker]

He told me he wanted a better proposal when I asked of he wants to marry me (after he asked) I'm 95% sure he'd say yes.

[abc3643]

The mere fact that you are asking these questions mean that you are not prepared to be married - period.

#1. First, when about to propose, you should know your partner so well that you can anticipate their answer to these questions.

#2. Second, if you were mature enough about love and marriage, you'd already know what I wrote in #1. But you didn't, so...

No. You should not propose because you are not there yet.

[Asker]

I asked because I’ve always thought it was better to leave it to the guy. My boyfriend basically told me to propose. I’ve always preferred more traditional gender roles so this is very far from my comfort zone.

[abc3643]

Well that statement right there tells me that you should not be married to him at this time.
You two have a difference of opinion on a fundamental aspect of relationships. You are bound to have more.

[Asker]

He explained how damaging it was to him when his ex turned him down. He straight up asked me if I’d say yes if he proposed and I told him yes. And yet he told me to instead. We’re in agreement on just about everything else.

[Wise4myage]

No, wait for him to do the asking. It will make him feel manly.

[Asker]

He basically told me to propose. When I said that traditionally the man does he said that women can too and told me what kind of proposal he wants. I usually prefer traditional gender roles so this is very far from my comfort zone.

[Wise4myage]

That’s lame.

[Asker]

He’s worth it but I still feel weird about proposing. Be so much simpler if he would but one of his exes turned him down.