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Welcome to Hump Day, where award-winning psychotherapist and TV host Dr. Jenn Mann answers your sexiest questions—unjudged and unfiltered. Have a quandary? Email us anonymously at HumpDay@instyle.com.

Dr. Jenn Mann
Dec 06, 2017 @ 11:30 am

DEAR DR. JENN,

I felt ready to get engaged to my boyfriend about six months after meeting him. Three years into our relationship, we're happy and both envision a future together, but I haven't gotten any indication of when that proposal is coming. I'm starting to become resentful and anxious. How can I help him feel ready or at least find some way to embrace uncertainty without sabotaging what I do have? —Ring Anxiety

DEAR RING ANXIETY,

You are in proposal purgatory, and this is a dangerous place to be. It sounds like your boyfriend has made it clear that he wants a future with you, but here you are, three years in, with a bare ring finger. What makes this a perilous position is the building resentment that tends to come with it. This animosity can be like poison to the relationship and can actually lesson the chance of the proposal—not to mention the happy, long-lasting marriage you're looking forward to. Nobody wants to propose to a partner who is seething with bitterness or as a reaction to being backed into a corner. You want to be honest about your desires, but you don’t want your boyfriend to feel like he is in a pressure cooker. That doesn't do much good for either of you. 

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The first thing you want to find out is what is holding him back. It sounds like he feels that you are The One but is resistant to taking that leap into matrimony. There are a few common reasons why men are sometimes slow to pull the trigger in situations like this. Once you figure out which is the culprit, you'll have a better handle on how to move forward. Here are the five most common proposal holdups I see in my private practice and how to tackle each one:

1) He is saving for a ring. In the age of student loans and credit card debt, saving up the standard two-to-three months salary is a tall order. If you believe this is what might be holding him back, let him off the hook by telling him that you would be happy with a smaller diamond or less expensive stone (emeralds and rubies are lovely!), want to use a family ring, or believe in skipping the engagement ring altogether in favor of going straight to a wedding band.

2) He has not accomplished his career goals yet. Many men have a vision of where they would like to be professionally before they walk down the aisle. He is unlikely to propose when he is in medical school, has just changed careers, was recently laid off, or didn’t get the promotion he was hoping for. Have a conversation about what he envisions for his career and what steps he feels are necessary before getting engaged, and then find out how you can best support him in achieving his goals. You may feel as though his professional and personal lives are intertwining but distinct paths that shouldn't dictate each other's timelines, while he may consider the two to be one linear path. If he expresses this, let him know that you want to stand by his side, as his wife, while he continues to kill it at work. Or ask him to define the career goal he wants to tick off before popping the question so that both of you know what he's working toward, and the goal doesn't continually shift as he climbs the corporate ladder. Either way, knowing what he has his professional sights set on will keep you from questioning whether there's something bigger behind his hesitation.

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3) He does not feel financially secure. Despite how much traditional gender roles have changed, many men want to feel like they are able to support both themselves and their partner before marrying, even if they will never actually have to take on that burden. According to a survey by the National Marriage Project, 47 percent of men want to be able to buy a home before getting married, and 40 percent want be able to afford a tasteful wedding party. If money is what's holding him back, sit down together and see where you can cut back expenses as a couple. Perhaps you can eat at home more often, go on fewer vacations, or find a less expensive apartment when your lease expires. Working together to achieve financial goals has dual benefits; not only does it save you both money, but having a common mission also brings couples closer together.

4) He's unsure about your future together. Of course, there is also the possibility that he's undecided about whether he sees marriage in his future with you. Is there an aspect of your relationship that gives him serious pause? If so, it's important to figure out whether it's something that can change, that he can learn to accept, or that will ultimately end the relationship. It sounds like this is not the case, but make sure that when you talk about your "future" together, your definitions of that word match. Some people don't feel the need to plan ahead; they are comfortable with the notion that something can make them happy for now—even for a long time—without wanting to commit beyond that. Others are all about long-term commitment but take issue with the legal institution of marriage. You would probably know at this point if your boyfriend were strongly opposed to marriage itself, sensing whether he's given the longevity of your relationship real thought is probably apparent too: Does he talk about growing old with you? Have you discussed the possibility of children? Is he comfortable when these topics naturally come up? If they do, this is probably not your problem; if they make him flinch, it's time for a larger conversation.

5) He's resistant to the reality of marriage. Sometimes people like the concept of marriage in theory but get cold feet about putting it into practice themselves. I see this most often among 1) men who were once playboys and struggle with the idea of letting go of their youth for what they perceive as a more sedate lifestyle and 2) men who grew up around bad marriages, i.e. those whose parents probably should have gotten divorced because things were so volatile in the home or whose parents did divorce acrimoniously. If that sounds like your boyfriend, the best thing you can do is help him get into therapy to work through the pain from his childhood that holds him back. He needs to do that healing regardless of whether of not he ever gets married.

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In the meanwhile, don't forget to focus on yourself. Too often, in merging lives with our significant other, we lose our sense of self. In your quest for wife status, don’t forget about your individuality. Continue to grow emotionally, spiritually, and intellectually. Nurture your friendships. Pursue your own career goals and aspirations. 

One of the most common questions I get in this situation is, “Should I issue an ultimatum?” I am not a fan of the ultimatum. You never want to feel like someone married you because you threatened to leave them. A proposal is a developmental step in a relationship. People need to grow into it, not be forced into it. Here’s the catch: You don’t want to wait so long that you become resentful and angry. If you reach a point where you feel obsessed and hostile, where you've explored the reasons holding your partner back but don't see a clear path forward, it is time to move on and say, “I love you and I thought we both wanted the same thing. I thought we were on a path toward marriage, but it has become clear to me that we are not. I really want to spend the rest of my life with you, but your resistance to taking that step makes me think that you don’t want that with me. Marriage is too important to me to give up, and I think it is time for me to move on.”

This is not a manipulation, a tactic, or an ultimatum—understand that. This is a real goodbye. You don’t do it to get a proposal; you do it to free yourself and move on. If he gets down on one knee and proposes right then and there (which is unlikely), then you can face that challenge and opportunity at that time. 

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But that's jumping ahead. It sounds like you and your guy are on the same page and some honest chit chat about what is holding him back could make a big difference for the both of you.

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