Are we ready for this?
6 Questions to Ask Yourself Before Getting Engaged
03.17.20

A happy, long-term relationship is subject to a certain degree of inertia: It will keep moving forward in a straight line at a steady speed provided nothing significant sticks out a leg and trips it up. At its best, the consistency of this evolution can be a symptom of the relationship’s health, a gradual buildup of affirmative answers to the question “are we ready for this?” that conceivably culminate in spending forever together–whatever that happens to look like. At its worst, it can mean robotically sliding into each consecutive milestone instead of consciously and thoughtfully deciding to pursue them.

Where milestones are concerned, getting engaged is certainly one of the big kahunas–not only because it means you’re engaged (!!) but also because it is typically the precursor to an even bigger–not to mention legal–commitment. It also happens to be top of mind for me because I got engaged last August and I’m getting married in June (if anyone has a good song suggestion for my father-daughter dance, please share), and it was around this time last year that I really started thinking about the emotional and logistical realities of what getting engaged would mean–for our relationship, and for me personally.

I knew in my gut that I was ready to take this step, but I also found it helpful to drill down on why in a less amorphous sense. It’s impossible to detail the ways in which doing so has made the experience of being engaged feel more intentional and therefore special without sounding like a total sap, so I’ll spare you that and instead share some questions I asked myself while standing on this particular life precipice. (Everyone’s questions pertaining to this topic probably look a little different, though, so let’s discuss further in the comments).


1. Why do I want to get engaged?

There’s a lot of cultural momentum around the idea of getting engaged and married, which is why it’s useful to distinguish between doing these things just because you think you should and doing them because they actually make sense for you and your relationship. If you want to break it down further, start by asking yourself why engagement and marriage, as opposed to a long-term partnership, is meaningful to you. Bad reasons to get engaged might include: thinking it will “fix” your relationship; fear of being alone; social pressure (i.e. from familial guilt, or from the fact that a lot of your friends happen to be getting married); wanting a wedding (for what it’s worth, I don’t think wanting a wedding is bad in and of itself–it’s essentially a party in your honor, which is obviously not without its appeal! But I do think the fantasy of a wedding can be powerful enough to temporarily eclipse the realities of what comes after). Great reasons to get engaged might include: the desire to establish an integrated life together in every sense (emotionally, legally, financially); the pursuit of another significant medium for growing closer to each other; the opportunity to celebrate your long-term commitment in a very tangible way.

2. Why do I want to get engaged to this particular person?

The answer to this question might seem a bit obvious in theory, because if you’re thinking about getting engaged to this person in the first place then you probably love them and want to hang out forever and ever and getting married seems like a viable path to doing that, right? But here’s a related sub-question to examine that impulse a little more deeply: Regardless of whether or not you love this person and want to hang out forever and ever, do you also want to change them? And I don’t mean change as in evolution or growth–the latter two things will happen organically–I mean it in terms of harboring a hope that the person you are with will become different in some fundamental way. If the answer is yes, then getting engaged–i.e. making a substantial commitment to the person they are now instead of the person you hope they might be–is potentially jumping the gun. At the very least, it’s grounds for initiating a conversation about what your expectations are.

3. How do I want to get engaged?

Though the traditional engagement model in which one person picks out a ring and surprises the other on one knee can feel pretty ubiquitous, the reality is that there are infinite ways to get engaged, and the only “right” way is what works best for you and your partner. If you have strong feelings about the way you want to get engaged, it’s important to communicate them. Do you want to propose or do you want to be proposed to? Or do you not want a proposal “moment” at all? Are rings going to be involved? What about family members? Private or public? Dancing flamingos or no dancing flamingos? (Just kidding.) (Or am I?)

4. Have my partner and I had conversations about all the BIG STUFF (money, kids, religion, politics)?

If you and your partner have been in a relationship for awhile, you’ve probably had conversations about some of the “big stuff” by default as a result of spending lots of time together. Maybe some form of religion is already a significant part of one or both of your lives. Maybe you’ve worked out a system for splitting expenses that seems to be working well so far. Maybe you’ve gushed about how cute it would be to have a kid with their eyes and your toes. The reality of how these things actually play out in a marriage can look pretty different, though. Have you talked about whether or not you want to have a joint bank account? Or, if you have kids, how you want to raise them spiritually and/or politically? Is it important to you to have a partner who shares the same believes in these areas, or are you content to disagree? If you’re thinking about getting engaged but haven’t discussed the nitty gritty aspects of these topics yet, I recommend opening a few bags of chips (for sustenance) and diving right in, no-holds-barred.

5. Is my “vision” for the future compatible with my partner’s?

I chose the word compatible very deliberately here, because I don’t think your hopes, dreams, and expectations about the future need to be the exact same as your partner’s–they just have to fit together, coexisting harmoniously, like two pieces in a jigsaw puzzle. One way of getting clarity on this is asking yourself what you want your life to look like in 10 years. Then ask your partner the same question and talk through any glaring sticky points.

6. Will I still be me?

Approaching a big relationship milestone is a unique opportunity to check in with yourself and how you are being impacted by your identity as part of a couple. Pursuing another step in the relationship can either be a conduit for moving closer to what you want for yourself and your life, or it can be a yoke–an added weight that slows you down from getting where you need to go. Take a moment to imagine what the fullest, most expansive version of yourself looks like, and determine whether that version of you can still exist when you embark into engagement land. Ideally, making permanent room in your life for another human doesn’t mean shrinking yourself into its narrowest iteration, it means exploring new avenues for growth together.

Did I miss any other important Qs? Let me know in the comments.

Graphics by Lorenza Centi.


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