How to Get Him to Propose

Are you in a long-term relationship with someone and want to know how you could get him to propose marriage? If you’ve already read Does He Want to Marry Me? The Dating with Dignity Guide to Getting Engaged and are wondering if there are any steps you can take to get him to go to the next step, you’ve come to the right place.

One thing is certain: dropping hints is NOT a good way to get him to propose. At Dating with Dignity we call this “leaking.” When a woman “leaks” without being direct, it can actually push a man away. Most men are on their own timeline and internally need to make darn sure they’re ready before popping the question. The reason? Although we might think that if he’s found “ the one” there should be no question about whether he wants to marry you, he has to be READY in the way that he personally defines “ready.”

So how to get him to propose?

Our friends at Glamour have suggested that you bake him a chicken. Here at Dating with Dignity, we have some alte ative suggestions.

Find out if he has realistic expectations of you and your relationship with him.

It’s important to note if your man knows that every relationship is going to have its own variety of ups and downs. If he thinks you should never disagree on anything or argue EVER, this is a red flag that he’s not going to be ready to propose anytime soon. He may be caught in the chase of perfection, unable to articulate what he wants differently or hoping, secretly, that maybe you will change to fit this idealized version of relationship.

Mature adults realize that no one person is perfect and that when you find a person who’s not only committed to the growth of the relationship but also sees value in growth itself rather than the destination of perfection, you’re both most likely to find marital bliss. As long as both parties have realistic expectations of how a relationship works, you’re on the right path to marriage.

If he’s working toward a professional milestone or goal:

Is it ever okay to give an ultimatum? If you think your man can’t see himself with anyone but you, but he’s currently focused on something like getting that big promotion or another professional milestone, it may be okay to give him a firm deadline of how long you can wait (i.e., when he gets the promotion, when he finishes business school, etc).

At the same time, open communication about marriage is the best way to get a feel for his views on it and when he might actually be ready for it. What’s essential is that you don’t imagine or assume you know how he feels or thinks about marriage, you or being “ready.”

Again, in that ideal mature relationship, communication is essential. Fantasizing that he “should” just ask you and that it will happen without your expressing that it’s important to you isn’t realistic. Make sure you can articulate why it’s important to you in detail; “just because it is” won’t cut it! Remember, life is not a romantic comedy or reality TV show, and most likely your proposal will not look like a scene from The Bachelor or The Bachelorette.

One way NOT to get him to propose: Repeatedly bringing up marriage in a snarky, sarcastic or back-handed way will not encourage him to bring up the subject. If you’re forcing your own agenda and timeline by mentioning that your best friend’s cousin just got engaged and that you’ve been dreaming about centerpieces for your future wedding, you’re setting up your man to run for the hills. It would be best to bring it up in an open and honest discussion and articulate what you want for your future, asking him what he sees for both of you.

If you feel like you have to pull some tricks out of your wedding veil to get your man to propose, chances are he’s not the one. And you’re welcome to try making “engagement chicken” in the hopes he will propose, but our Dating with Dignity advice is to skip the chicken and go for communication.