How to Discuss Engagement without Ruining the Surprise

Couple sitting on floor and talking

Many couples abide by the tradition that a man asks a woman to marry him, often with a particular display of affection and the presentation of a ring. Regardless of whether all aspects of the tradition appeals to you, it can be a fun opportunity for one person to plan and execute a fun surprise, usually demonstrating their thoughtfulness, love, and good memories.

The problem with this, of course, is that it risks surprising the other person so much that they say “no” or “I’m not sure,” simply because they’ve not yet thought about the possibility. Much like lawyers asking witnesses questions in court, people who are proposing want to know what the answer to the question “Will you marry me?” is before they even ask it.

One of the best ways to avoid the awkward situation of a surprise proposal rejection is to have an honest talk about the relationship with your significant other before you consider getting engaged. Below, consider some ideas for both the “proposer” and the “proposee,” to make sure everyone is on the same page even if the engagement time and place itself is a complete surprise.

Couple sitting on beach and talking

Ideas for the Proposer

If you know you are ready to get engaged, think carefully about your partner’s attitudes: do they seem to reference future times you will be together? Do they behave in a way that makes them seem ready? Look for moments when they reference times you will spend together months or years out; think about times you’ve daydreamed about children, careers, or moves that would take you to the same places or into the same adventures. These kinds of signs might mean its time to initiate a talk about engagement and where your partner sees him or herself.

One easy transition moment is when discussing these same kinds of future plans: if one of you is talking about a job, an apartment, or a community where you live, a great discussion point is to talk about where you see yourselves living, working, and participating in the next five years. During such a discussion, it can be valuable to mention that, by a certain time in the future, you see yourselves as being married. This isn’t a proposal, especially when it is framed in terms of years away, but the reaction you get from your partner is a great way to gauge where they stand on the issue. If they seem hesitant, ask them to share their thoughts on marriage and timelines for it.

Another option is to ask your partner to think about when they see themselves as being engaged and when they see themselves getting married; you can ask in a way that allows them time to think about it and possibly write their answers down rather than speaking them out loud. Getting this information can lead to some surprising talks (not as surprising as a proposal rejection, but still raw), so prepare yourself to honestly and compassionately hear if your partner isn’t ready for engagement or marriage.

Older couple talking on a couch while drinking tea

Ideas for the Proposee

If you have been thinking that it is almost time to get engaged, there are direct ways for you to talk to your partner about engagement without frightening them off. Starting a conversation can be totally hypothetical, and you can let the other person know from the beginning that you aren’t putting pressure on them to start moving toward engagement right now.

One valuable question for proposees to ask is, “What obstacles or barriers do we need to overcome before getting engaged?” You can ask the question outright, or you can find an online quiz or list of questions to talk through. Important points like being on the same page about future children, where you want to live, and what kind of work you want to do should be in the equation. Even if a proposal itself may seem like it is all about romance, these practical obstacles and barriers should be addressed first, rather than just hoping they will “work themselves out”.

When you have the answers to these questions, it is completely fair to let your partner know your ideals in terms of when you’d like to be engaged and married. What is important is to make them confident that you aren’t making an ultimatum—ask me within a year or we’re over—and that you care more about them being comfortable and ready than you do about the actual timeline. Obviously, if you have been waiting a very long time and continue to feel like engagement is long overdue, that is an important conversation to have as well, but rarely do ultimatums result in romantic engagements and successful marriages.

Another move for proposee success: if your partner is reluctant to discuss engagement or get engaged, ask if he’d be willing to talk it through with a friend who is married already. Perhaps your partner is nervous about long-term commitment and gets too flustered to discuss it well with you, but with a friend who doesn’t expect anything from him or her, your partner might feel more open and able to talk about the worries of the situation. Wanting what is best for your partner will help you to both express what you want and give him or her time to think.


Through these strategies, you and your partner can get on the same page before a romantic proposal moment happens. Once you’ve had this talk, the proposal becomes even more auspicious, since you know it could happen but don’t know when or how it will happen. If anything, knowing when you’ll be ready for engagement makes the proposal all the more wonderful and exciting, even if you aren’t completely stunned that the thought would even cross your partner’s mind.

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