Commitment Dating and Romance

How to Set and Communicate Your Dating Goals and Timeline

What if you could almost magically get PERFECT CLARITY on the future of your relationship?

What if you never, ever felt like you were waiting and wondering if your boyfriend would move with you to the NEXT level of commitment?

It would be awesome if this kind of thing “just happened” on it’s own, just like it would be awesome if you and I could have dark chocolate cupcakes soaked in Gran Marnier and frosted with maple buttercream icing for breakfast every day this week and not give a thought to how well our jeans fit. 🙂

The good news (think of it as maple-frosted news) is that you CAN get perfect clarity on the next stage of commitment with your man.

And you won’t scare him off, or set off any drama-bombs.


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With what I’m about to tell you, you will understand SO WELL exactly where the two of you are and are heading, it will be like looking into a relationship crystal ball…

“Hi Claire, I have been dating my boyfriend for a year and a half. He says he loves me, wants to spend his life with me, and he wants me to move in with him. BUT he knows I won’t live with him unless we are at least engaged. He says he’s not ready to propose. He has plenty of reasons, he was married before, needs to be sure, he’s afraid he will disappoint me, etc… I love what we have, but I am starting to itch. Do I give myself a deadline? Do I tell him about the deadline? My biggest fear is: if he’s still not convinced – who says he ever will be?” – Cammie

Yes, girlfriend, you are exactly right: You need to decide your timeline, and communicate it to him. After I explain HOW you do this, I’ll tell you why this simple act will completely change your life for the better…

1. Name your milestone(s)

First, figure out your main commitment milestones. Like becoming exclusive, introducing him to your kids, getting engaged (that’s yours, Cammie), moving in together, getting married.

Easy as licking frosting off your finger, right?

2. Figure out your dating timeline

Now answer this question: “How long am I willing to date this man before I decide if he’s the one who will [insert your milestone] with/to me?”

Maybe your timeline is 3 months, 8 months, a year, or even two years.

3. Communicate your timeline with him, and ask for his input

First, choose a good time. Low stress, no interruptions, a happy place for both of you. Then, recount some of your history together – the good stuff!

Now you are ready to communicate your timeline.

FOR EXAMPLE: Francesca is casually dating several guys right now, but wants to be clear that she HAS a timeline.

“I’m very serious about finding the man I want to spend my life with… I think I’ll know within [insert the timeline] of beginning to date someone whether or not he’s the one. What about you? How long do you date before you decide whether there’s a future for the relationship?”

FOR EXAMPLE: Emma’s been dating Elijah for 7 weeks. She wants to become exclusive.

“Someday, I want to stop dating other guys so that I can begin building a relationship with the one man who makes my heart sing. I probably wouldn’t date a guy for more than 3 months if I knew we would never become exclusive. What do you think?”

FOR EXAMPLE: Martina has been dating Mateo for 1 year. She wants to become engaged.

“We’ve been dating for a year and I think we make an amazing couple. I feel like a couple will probably know after a year and a half whether or not they want to get engaged. How does that match up with what you’ve always thought?”

FOR EXAMPLE: Zoe has been dating Caleb for 6 months. Someday she wants to be married.

“I want to be able to wake up every day to the man I love. I’d like to be there for him when he needs me, and know that he is there for me no matter what. I enjoy having a boyfriend, but I don’t want to have a boyfriend – even one as marvelous as you – forever. I want to get married one day. Not right now, but probably in the next three years.”

See? Not so hard at all! It’s entirely possible that he will be very open to hearing you, and thinking about what you want.

It’s up to you to keep the ball from being dropped, though. So communicate, communicate, communicate! If you REALLY want to get engaged (or meet a particular dating goal), and you know your general timeline for that, keep taking baby steps forward.

MORE: How to Talk to Your Man (about ANYTHING) and Get the Answers You Need

What to do if he says “I’m not ready!”

That’s okay. This is simply the first part of an honest struggle. And he’s communicating with you, which is a GOOD thing.

He may already KNOW that he doesn’t want the milestone you want. He may hope to keep things like they are, and not move forward.

Now you know, and you can get started thinking about how you’ll respond.

Or he may react negatively because he’s scared. You can work with that.

Invite him to share some of his fears, because fears should be heard out, but they don’t have to be the last word. And the two of you can get help moving through them. Because that’s what great relationships DO; they move through things.

Your goal here is to be understanding, but also set up a time to talk about it again. Communicate that like so:

“I understand. Everyone moves at their own pace. Let’s talk about this again next month.”

In other words, definitely set your sights on this man. For now. But don’t pin everything on HIS decision, because it’s YOUR decision too, beautiful.

No matter what happens, you’re in charge of your own life, and you are showing that you respect and care enough to communicate with him, and you also place a high value on your needs and goals.

At some point you might want to break the arrangement the two of you have in order to move on with your life. Or maybe you extend your timeline because he’s trying really hard and has said 3 more months would really be helpful.

But either way, you’ve decided your own timeline, you’ve communicated well, and there are no “gray” areas so you’re not stuck wondering. Which makes for a MUCH better, clearer life.

xoxo Claire

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4 comments on “How to Set and Communicate Your Dating Goals and Timeline

  1. Theressa

    Girl you must be living in a different world than I am. There’s no communicating with men in this society, at least not in the 50 to 60 year old world. I’ve had at least 200 first dates in the past 3 years. Some second dates, and third. But if you don’t put out on the 1st, 2nd or 3rd date your done. Then if u do enter into dating for awhile the very 1st time u express ANY expectation or discontent u a setting yourself up for loosing him. I’m no slob and I don’t bend to “his” every wish but I can’t for the life of me figure out how any of what u are saying fits into today’s dating world! These men are broken and they are not making any attempts at communication. They want to be completely untethered with no demands on their time and space unless they volunteer it! I’ve been back to dating for 4 years now and the horror stories never end, even when u r under the delusion that this one looks hopeful!

    • Claire Casey

      Wow, Theressa, your situation does sound discouraging; I’m sorry to hear that things have been going this way for you. I’m hoping you have a support network of wise friends and mentors who have healthy relationships and can help you figure out how to navigate the dating scene you’re experiencing…

      Wish I had a magic wand for you, girlfriend… Hang in there and stay strong. Not all men are this way, but it sounds like you’ve encountered more than your share.

  2. Yes Theresas is correct.
    The advice given is usually directed to a much younger group. At 60+ I can tell you, it’s a different world. They want younger women and there are 2.3 women for every man.
    Claire, you can’t advise her because you can’t relate.

    • Claire Casey

      You’re definitely right in that I’m not 60+ and dating. 🙂 And I’d love to hear your advice for communicating with guys for the 60+ crowd, if you’re interested, Judy. I plan to also ask some of my girlfriends who are successfully navigating the dating world in that age group right now (and I will try to ask some guys as well).

      I’m not willing to say, “It just can’t be done at all!” but I know there are special challenges. Feel free to email me at Claire [at] AskClaireCasey.com if you like, or just leave me your pointers here!

      Thanks for taking the time to read and comment, Judy.

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