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Ron Simms Jr.
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Ask MISSter Simms – My Boyfriend Won’t Propose!


Desperately seeking wedding vows

Dear MISSter Simms

I’ve been living with my boyfriend for several years now.  We share a house together as well as our finances, are deeply involved in the lives of each other’s families, and also have a pet together.  We were going to get engaged, but my boyfriend has some lingering issues from a bitter divorce his parents went through when he was a child.  He started seeing a shrink to deal with his issues.

Fast forward six months, and he’s finally making some progress.  I hated that I had to delay my engagement, but felt it was worth it if we were both in a place where getting married didn’t seem scary.  Things started going so well, that he took me out to go find a ring.  It was great!  He got me something really beautiful, and I couldn’t have been more thrilled.  But all of that changed when, instead of proposing to me like I imagined he would, he claimed he wasn’t ready to be engaged to me and that he wanted to break up.

We patched things up after a lot of talking (and even more crying), but where do I go from here?  I want to marry him, but he’s not even close to ready.  The real problem, though, is that nobody really knows why he doesn’t want to get married.  Am I being foolish in even trying to get him to marry me in the first place?  You would think, after being together for so long and going through therapy, that he would be able to do it.  But now we’re back at one.  I’m not sure how long I can wait, but I don’t want to rush out of this relationship that has otherwise been great!  What should I do?  Help!

Marry Me!

Dear MM,

You’re right.  After living with your boyfriend for five years, and supporting him through therapy, you would think your boyfriend would be ready to marry you by now.  Yet with every passing day the chances of you guys getting married seems to be getting slimmer and slimmer…like Kate Moss during her heroin chic days.   If you’re pinning all your hopes and dreams on you’re man waking up one day and finally deciding that he’s ready to marry you, you might want to stop now before you wind up even more disappointed.

To me, you’ve got two choices:

1. Stay with your man – My dad used to always say, “Why buy the cow when you can get the milk for free?”  He grew up on a farm, but what I think he meant was. “Why marry the girl when you’re already living with her and are kind of in a marriage anyway?”  You live with your boyfriend, share bills with him, are all up in his family’s business…sounds like a marriage to me!  Only thing you’re missing is a big, bling bling ring and a piece of paper making everything “legal”, but who needs that kind of stuff anyway?

2. Leave him – If marriage is that important to you at this point in your life, and your man is unable to provide you with what you want, then it might be time to get the heck out of Dodge (which, I just learned, is in Kansas).   He may realize how much he wants to be with you, snap out of things, and finally come around to the whole marriage thing.  However, he may not.  If you leave him, you just have to be prepared for a future without him and know that you can still get married, just not with him.

I say give it one last go, and if it doesn’t work out again, you’ll know for sure that it’s time to move on.

Need relationship advice?  Send your questions to ronsimmsjr at gmail dot com and you might be featured on the next installment of Ask MISSter Simms.


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