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Dear Wendy: “It’s Been Five Years And My Boyfriend Still Won’t Propose!”

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I’m a 27-year-old female, and I’ve been with my 31 year old boyfriend for over five years now. We have made a happy and loving life together, including sharing a home, sharing our finances, being closely involved with each other’s families, and we even have two cats and a puppy together. About a year ago we started talking seriously about getting engaged within the next six months, but by the time fall rolled around, my boyfriend told me that though he loves me and wants nothing more than a future with me, he was just not ready for an engagement yet. He had some issues from his parents’ divorces, and decided to begin counseling to deal with them.

He has been making great progress over the last six months, and though it has been difficult to delay our engagement, I truly felt it was all worth it to make sure we’re both in the right emotional place. Finally, he felt that he had “gotten there” emotionally, so last weekend he took me ring shopping, and we picked out a beautiful engagement ring! He even told me he would propose within a week. Well, instead of proposing, he absolutely shocked me by announcing that, though it would break his heart to do so, he thinks we have to split up because he’s still not ready to get engaged.

This weekend we talked and cried, and ultimately decided to try to work through this. But I am at a loss as to how to actually do that, because he has no idea why he’s not ready to get engaged now. How can we do this if he can’t even identify what is stopping him? I want to give him more time, but at this point, am I being foolish for thinking that he’ll ever change his mind? I thought that months of counseling (after over five years together!) would do it, but it feels like we’re back at square one. I don’t know how much longer I can wait for him to be ready, but I hate the thought of giving up on a relationship that is so amazing in so many other ways. Should I just cut my losses and MOA? — Tired of Waiting

If your future happiness is contingent on getting married, I would cut your losses and MOA, because clearly there’s absolutely no promise of that. On the contrary, the chance of marriage seems to be getting slimmer with each passing month. It’s been five years, after all. He’s had six months of therapy! And still, he is no closer to marrying you than he ever was. Furthermore, he doesn’t seem to even respect you enough to give it to you straight. He keeps letting you believe that he will change, and he won’t let you go despite knowing that he is unable to give you the thing you desperately want (marriage).

Well, if the risk of divorce is scaring him much more than the risk of losing you — or if his fear of commitment is bigger than the fear of losing you, it may be time to show him exactly what losing you would really feel like. It might be the only way for him to finally reconcile what the biggest risk really is. But if you do leave him, you have to understand there’s a risk for you as well, and that is that he won’t be the only one to lose what he loves the most. But in the end, as heartbreaking as it will be, leaving him is probably your best chance to get the marriage you want eventually. You just have to accept that it may not be with him.

If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com.

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