How to Handle Distance and Obstacles in Second-Marriage Dating

How should people handle practical obstacles in second-marriage dating?

Practical obstacles such as distance, work, housing, and adult children deserve serious attention, but they do not always need to be solved before two people know whether the relationship has genuine potential.

I recently worked with Debbie and Zev, who were each looking to make a commitment to someone for a second marriage. On paper, the match looked wonderful. They had similarities in their backgrounds, their interests, their ages, and their wishes for the relationship. But there was one potential problem: They lived two hours away from each other. When I floated the match, both brought this up as a major challenge. Both had good jobs in their current locations. Debbie also had two unmarried adult children still living at home. Where would they live? How would they make it work? To them, the problems it posed seemed insurmountable. My advice: Why didn’t they at least try meeting first? That way they could see if there was even a point to worrying about the distance. After all, it wasn’t going to matter if they didn’t like each other and feel like they had chemistry.

They agreed. And they really clicked.

But they still had that big problem to deal with: distance. Both got back to me that they didn’t think they could overcome this challenge. What should they do?

Again, my advice to them was simple and straightforward: keep going. See how things progress. Often, these things tend to work themselves out over time. Lo and behold, they are now married! Zev took such a great liking to Debbie that he moved to her location, works remotely most of the time, and commutes twice a week. They even both kept their houses. For Zev, he realized that being with Debbie made him so happy that it was worth the sacrifice. Moreover, it may just be a temporary sacrifice because her children will move out eventually. And then they may reevaluate their situation. Why does “just keep going” work?

Relationship Problems Often Change in Size and Severity Based on Context When Debbie and Zev saw their distance from each other on paper, it automatically felt like a deal breaker. After all, why start a relationship when you already know there’s a problem? So why did I encourage them to keep going? Because sometimes “insurmountable” issues can start to look smaller and smaller when you weigh them against all the good things that draw the two of you together. This isn’t to say that you should ignore potential problems. They will eventually need to be addressed. But it’s okay to let this happen naturally as the relationship progresses. To see if the initial chemistry you feel blossoms... or fizzles. Who knows—there may be other hurdles that appear and derail things.

But if you have commonalities, a similar background, and that “spark,” what seems like a big deal at first may really not be. Time—especially when spent together—does its own thing. What the brain cannot do sometimes time will do on its own. It has a way of fixing things. Of offering solutions that didn’t seem feasible at first. Of allowing you the space you need to talk things through. These are rules that apply regardless of whether you’ve been married before or not. The key to finding happiness with someone is often to just keep going; keep spending time together, keep talking things out, keep learning, and keep listening. As long as you can do those things together, you’re headed in the right direction.

Frequently Asked Questions

When should a couple solve a practical dating problem?

Clarify the immediate decision first, then address larger logistics as the relationship develops enough to justify those choices.

How can couples apply this insight?

Begin with one calm conversation and one small, repeatable action. Focus on the shared pattern rather than blaming either spouse.

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