How to Set Up Your Long-Distance Relationship for Success

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Hey Wendy,

I’m dating a wonderful man who lives in LA but is in NYC almost every week for business. I live in NYC.

This is our 2nd time around. I broke up with him 6 years ago because I didn’t want to be in a long-distance relationship with someone non-committal. However, during the past 6 years I’ve dated men in NYC and even in my own zip code but they might as well have been on Mars—unavailable and non-committal.

This time I am more open to exploring our connection, because I do really like him and enjoy his company, and he’s a gentleman. We are compatible intellectually, emotionally, and physically. This is the closest I’ve felt with anyone in a long time. I also have a full life with lots going on and it might be a good thing that I’m not consumed by this relationship.

He’s a great communicator, but when he’s not in NYC, he disappears. He needs his space. He is immersed in his start-up business. He texts almost every day but does not call much.

It’s been a month since we’ve been dating again. Is it too soon to freak out and feel like I should be asking for more? Or should I let things unfold and see if it feels good or not? I’m in my 50s and he’s 60.


Hey M.R.,

It’s heartening to hear you’re giving this guy another chance. Now you’ll be able to see with eyes wide open if you can get enough of what you need from him to be happy. Relationships are not one-size-fits-all and today, we get to design our relationship(s) any goddamned way we want to—especially when we’re of a certain age.


I would pay attention to the substance of your connection, not the form society thinks it has to take. The pressure to conform is real, and many think that a serious relationship has to follow one path: dating, acceleration of frequency and communication, exclusivity, moving in, a wedding, and “till death do us part” etc. That is certainly one form, but it’s not the only path.

So instead of titles like “are you my boyfriend?” focus on what you’re building together (which sounds like the potential for deep and intimate connection) and on all the ways he makes being with him better than being alone. Pay attention to what he brings into your world, how he makes your day brighter, and how you’re a better person for knowing him.


Next, look to your needs. When you don’t hear his voice, does that make you feel off-balance? Or do the texts give you enough connection to tide you over? Whenever I’m trying to sort out my emotional well-being I look at the situation from two places: 1) What would it look like if I had it all my way? and 2) What would it look like if I had “enough”?

The first is easy: all my way includes hopes, dreams, desires, and even unrealistic fantasies. The second, “enough,” is also easy: notice what makes you upset, and that’ll give you what’s not enough. What would need to shift from “I’m upset” to “I’m alright”? What’s fine is a perfectly solid goal to aim for when you’re looking at what’s enough.

When you’ve sufficiently navel-gazed and figured this all out, you can bring it to him. You could start by saying something like, “I like what we have, and I’m glad we’re giving it another go. I can totally respect your need for space as you build your start-up, and even after that, if you need. Now, can I share my thoughts about what I need in return to set us up for success this time around?”

Once he’s bought into having this conversation, you can share with him your baseline of enough; what you’d need to be in good emotional shape during the gaps you’re not together physically. And from there, if he’s willing to provide the baseline, you can thank him for providing that and let him know how awesome it is that this could work out.

Then you can say, “No pressure here, but can I share with you what life would look like if I had it all my way?” And as you share, watch what parts he’s a “yes” for and where you feel his resistance.

You are sharing here, and ultimately you are accountable for your own feelings. But you also want to give him the opportunity to contribute to you and your emotional well-being. It’s not semantics, it’s interdependence, and when done right, it’s lovely.


Exclusive, not exclusive, going up the relationship escalator, or staying right where you are together now—are all valid forms of relationships.

So, when it comes to answering the question, “Where is this going?” what do you need from him? Do you need to be married? Do you need to live in the same city? Or is what you have now perfectly fine for you for the long haul? Only you know the answer.

I will assert my own personal opinion here. I believe that (generally) a person who plans to be in a long-distance relationship for more than one year should not be exclusive. It’s not fair to anyone to put dibs on someone’s time when they’re not available and/or accessible most of that time. It’s a setup for disaster later on.

So, can you do it? Can you be in a permanent, long-distance relationship with someone great and still get all of your baseline needs met? Maybe so, maybe no.


I’m glad he’s a good communicator since you’ll need that. His “disappearing” and texting vs. calling you is not alarming to me. Many men need that kind of singular focus, and context shifting is real. And I understand your annoyance by it, because as the masculine needs single focus, the feminine feels most safe when we are connecting, and these two needs collide in midair in relationships around the world every single day. So, know this going forward and work out what you need (baseline) for connection time, while honoring what he needs for focus time.

I truly wish you two a happy life together.

P.S. If you have my book, 121 First Dates, please read the chapter on long distance. I have a lot more to say about how you can get your needs met and see all of who he is when you aren’t in the same location for more than a few days in a row.