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Online Dating Magazine > Columns > Date & Relate > Dating an Ex

Date & Relate
by Sara Hodon

Love the Second Time Around
Dating an Ex

You did it.  You’re back out there.  You’ve moved on.  You’re ready to find someone new and start the next chapter of your life.

So you’re as surprised as anyone to find yourself back with your ex.  And even more surprised to find yourself with someone who is your ex, but they were several exes ago!

Before you start thinking there’s something seriously wrong with you, don’t panic.   As exciting (and tedious) dating someone new can be, there are certain loves from your past that find their way under your skin and into your heart.  And no matter how hard you try, they stay there.  It’s not unheard of to rekindle an old (or not so old) romance.  Sometimes being in love with a person you dated in the past is even better the second time around. 


If you are considering trying to rekindle some old embers, keep these words of advice in mind: 

  • Put some distance between the old relationship and the new.   
    Sure, there are more than a few “on again, off-again” couples out there, and you may have been part of one.  I find that many of those high maintenance couples thrive a little bit on the drama of making up and breaking up.  That may not be your style.  If you’re seriously trying to work things out with your ex and keep things as drama-free as possible, give yourself some time to think things over (and encourage them to do the same) and figure out if reconciling is really what you both want. 

  • Clear the air. 
    Talk about issues you may have left unresolved.   Don’t let them become an obstacle this time.   Getting rid of the old baggage and hard feelings will help you get closure and get ready to give your partner a second chance.  Perhaps one of your biggest pet peeves about the other person was something you never pointed out, and it’s something easily resolved (i.e. they snored). 

  • Start fresh. 
    Fall in love with each other again.  Start from the beginning—phone calls, going on dates, planning romantic weekends or road trips.  Go back to the little rituals and routines that you used to do together, and don’t forget to start some new ones to keep it exciting. 

  • See them as they are now, not who they were then. 
    Depending on how long it’s been since you were with the other person, respect the changes they have made within themselves and within their lives.  Remember—you’re not the same person, either.  And don’t forget to ask yourself the real question—could you fall in love with this new and improved version of your old flame?   They may have made some radical changes in their lives since you last dated.   Perhaps when you met them, you were attracted to their relentless drive to succeed and ambitious nature.  Now, they’ve given up the high pressured job in favor of a simpler, less frenzied lifestyle.   Is this something you can live with?   Maybe your former grease-and-beer loving boyfriend has turned into a radical health nut who never wastes an opportunity to point out the unhealthy toxins you regularly ingest.    Don’t try to rekindle your old romance hoping they’ll revert back to the person you knew. 

And you’re right to be cautious, too:

  • Don’t “settle” because it’s more comfortable. 
    They know your morning routine.  You know they arrange their closet a certain way.  You had your favorite restaurants, ways to spend a lazy Sunday, and you were each other’s “other half”.  Who wouldn’t want the comforts of a solid, established relationship?  Sure, it’s great to have someone who knows you so well.  But keep in mind that it ended for some reason.   Were you truly happy with this person, or are you just going back to them because it’s easier than starting over again?  If you do give it another try and find you’re just as unhappy this time around, don’t waste any more time.  End it. 

  • Remember why it didn’t work in the first place.   
    You were ready for marriage and they weren’t.   You constantly fought over money (or the future, or whatever your issue was).   You are ambitious and goal-oriented, while they are content to barely make enough to survive or have you support them altogether.   These are common deal-breakers when it comes to lasting relationships.  If you experienced any of these issues the first time, chances are, they’ll resurface again (barring some huge life-changing event.)                           
  • Don’t be too quick to believe that “I’ve changed.” 
    There’s a saying that goes “You can’t change people.  You can only change the way you react to people.”  And it’s true!   People tend to show their true colors fairly quickly.  If your partner cheated on you, I’m wary enough to believe that it can happen again. 

  • Watch for backsliding. 
    If you do work things out and get back together, be watchful of old bad habits that might sneak back into your relationship.  If they liked to hang out with the crew and it was a major sticking point for you then, talk it over if that behavior starts creeping back. 

Finding true love is all about moving forward.  Sometimes it means going back to correct mistakes so you can move on.     


Date & Relate is published every Thursday by Online Dating Magazine columnist Sara Hodon. She can be reached at

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