Valentine’s Day can often be “make it or break it” time for a relationship. Those who aren’t invested enough to buy a present will mysteriously go silent at the beginning of February. On the other hand, those who are dating multiple people will try to keep things going a little while longer when the holiday falls during the week by booking one Valentine for Saturday night and one for Tuesday. Eventually though, that moment will come when you both start to ask where the relationship is headed – are we exclusive?

There’s really no great way to have this conversation. It always seems to come either too late or too soon, and rarely are you both ready to take the plunge at the same time. If you’re wondering, here are some hints that it’s time to have the talk:

  1. Your spare toothbrush moves into her apartment
  2. Your friends start checking her out and asking “what’s up with you guys?”
  3. Your boss needs you at a business dinner. He tells you he’s bringing his wife and you are welcome to bring a guest too
  4. You haven’t gone a single day without talking to one another in the last two weeks
  5. Mom is coming to town and wants to meet him
  6. You’ve lost interest in returning the other guy’s calls

If those statements sound familiar to you, it’s time to start thinking about how to bridge the topic.  Many traditionalists think it is up to the man to start the conversation, but if you are a woman who can’t handle the suspense of not knowing, it’s better to bring it up and see what he has to say instead of writing the imaginary script of what he’s thinking in your head. Here are some ways for both men and women to get the dialogue going.

TELL THEM YOU TOOK YOUR PROFILE DOWN – This is a clear sign that you are not looking for others and their response will tell you a lot about how they see you. If their reply does not include a similar statement, or a pledge to do the same, then you have to have another conversation about where things are headed. Just because they are not moving as fast as you are, doesn’t mean that the relationship is doomed. However, if he sees you as a goodtime gal and you want him to be your hubby, this would be a good time to jump ship before deeper feelings develop. Men generally categorize women quickly. You are either “DTF” or you’re a “wifey” as our Jersey Shore friends would say. And if you are “DTF,” they probably aren’t going to be introducing you to their mother any time soon.

DO THE OPPOSITE – If you’ve fallen into a pattern of casual dates, step it up a notch. If you have been on a series of extravagant nights out, plan to make her dinner at home. Switching up the routine and making that date feel different sends the message that the relationship is changing. Setting the stage for you to say, “I feel like things are getting more serious between us and I’m happy about that. What are you feeling?”

GET OUT OF TOWN – Going away together can be a big step in the relationship. Is there a place that you have always talked about visiting that is just far enough to do in a day trip?  Suggest you take the trip together, but before you go, say that you need to know if they are on the same page about what that means.

You do not want to have this conversation if you are tired, drunk, on the phone, or in a public place. As much as it might seem like you are seeing things the same way, sometimes you will find out at this point that they have different goals than you do. If the talk doesn’t go your way, remember that dating someone who is not on the same track as you will only block you from finding someone who is right for you. It’s better to hear the bad news than to fool yourself into staying in a relationship without a future.

If you are the one that wants to end it, remember that honesty is the best policy and a lack of response isn’t a response. The world is too small to just not return phone calls, inevitably you will run into her or him at temple or meet a cute friend of theirs who already heard about what a jerk you are and you’ll be forced to face the music then. Music usually sounds better live than it does in a recording, doesn’t it?

Dear Mrs D is an online dating strategist who conducts one-on-one coaching sessions and workshops for singles on how to find success dating online just as she did. She has been seen on Fox, NBC, and CBS and has written an ebook “D is for Dating: A Guide to Successful Online Dating” which is available exclusively through her website
  1. Dear Mrs D,
    Thank you so much for this insightful and timely article. I get hot & cold messages from my guy, which makes me hold back my heart. Sometimes we’re close, sometimes he can be quite distant.

    His wife passed away 18 months ago and I too am widowed, but for longer. How do I tell whether his keeping me at bay are due to me not being “the one” or grief? How long do I give him before I cut my losses & move on?

    Mrs G

  2. Goodwoman Mrs G – Thanks for your comment. It’s hard to put a timeline on healing from something as tragic as losing your spouse. My best advice for you would be to be honest with him and let him know how you feel. There is no magic time when he will suddenly get over his loss but knowing that you care for him and see him in your life in a meaningful way could help him become more committed to you. Feel free to reach out to me through my website if you’d like to continue our discussion and hear more strategies for starting that conversation with your fellow. Good luck!

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