Dear Preston: My Boyfriend Won’t Propose

Cute Disney Ride Wedding Proposal

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Dear Preston,

I’m a planner, and I love what I do. I also live with my boyfriend. We’ve been together eight years, and he’s my best friend. He is very supportive, and I love him. I know he feels the same way. And yet he won’t propose. I’m afraid that if I give him an ultimatum, he’ll leave. I know that marriages can fail; a lot of the weddings I’ve done over the last few years have already resulted in divorces. But I don’t care. I still want to marry him. My friends say I have to give him an ultimatum. But I’m afraid. What should I do?

Always a Planner Never a Bride

Dear Always,

I think it’s time you did some soul searching: do you truly believe in the commitment and importance of marriage? Or, are you just being pressured by your friends? After all, the commitment of marriage is not for everyone. You need to have a a serious heart-to-heart with your boyfriend. Tell him how you feel. Find out why he “refuses” to propose. He may be trying to save up for a ring. Or maybe he wants to get a little farther in his career before you marry and start a family. There are many reasons he may be hesitating that have nothing to do with you. You owe it to him and yourself to find out what those reasons might be. If he really is as supportive and loving as you say, he’ll be open and honest with you about his reservations. Good luck.


Dear Readers, what do you think this planner should do? Have you ever been in a similar situation?

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  • Events by Doyin

    Great advice Preston! She needs to sit down and have a talk with him on why he hasn’t proposed to her. He may be saving for the ring or may not just be ready for marriage.

  • Vanessa Alce (I Love My Planner)

    Friends are a great support system. But sometimes, we have to really be careful with how we listed to their advise. I’m speaking from my own experience. Giving her boyfriend an ultimatum may not be the best option. Preston, you’re right! This couple has to sit down and truly have a heart to heart about their relationship and where each of them see it heading in the future. After they’ve discussed it fully, she should make a decision that is best for her, putting aside all ‘friendly’ advise and external noise.


    I have to say something here to the future bride!
    Ask him if he ever sees you married? If he sees a future with you in it or not?

    Ultimatums are demands. Men hate that. They want to be the ones to decide if and when they will propose. They need that decision to be theirs. Do NOT try to coerce him to your image of your future, just ask what he sees and if its with you.

    He will tell you the truth.

    Also, do NOT be afraid that he will leave. Do not be afraid because if he doesn’t want it, he’s not the one for you.

    He should be the one afraid you will leave and trying to keep you!

    If he says he sees a future, ask when he sees a marriage. If you’re fine with that timeframe, ok, if not, tell him you see yourself moving on to start a committed family life before then.

    You must have the truth for him or you must start looking for rentals and dating websites. Either way, you will eventually marry Mr. Right, if you give yourself the chance and stop letting time pass you by! You can be planning your wedding with this guy, or you can be meeting Mr. Right but don’t wait around! Good luck!

  • http://YOURWEBSITE Jessica

    I believe a huge mistake women make is living with their boyfriends before they are married. They believe the lie that “they’ll get to know each other better”, so they can see if the marriage will work. This trial period of playing house allows people the mindset that if it doesn’t work they can just walk away. It is extremely difficult the alter that mindset. And, on top of it all, there is no longer any incentive for the man. He is comfortable the way things are and she is left to dream of “when”. Hold your ground, ladies. Don’t move in and he will get the ring.

  • Joyce

    I am in the same situation, always a planner but never a bride, we even have a 10months old baby girl, HE IS COMFORTABLE, my mistake was to move in together before the ring.

  • Ruchi oswal

    I love and agree with your answer. Could not have said it better myself.