Then Jack Happened


Dear Jack,

I’m having an issue with a long distance relationship.  I met a woman when I was working overseas and we spent a few months together before I had to move back to home base.  I wrote her a letter letting her know that I had strong feelings for her and she seemed receptive.  We kept in touch and decided to meet in another city for a long weekend.  It was like a honeymoon the first three nights, but then things fell apart on the final night.  We were in a small group of friends, and we couldn’t decide on what to do.  I was absolutely fine but she kept asking me what was wrong with me.  I wasn’t sure if I had the stink face on and reassured her that I was fine.  Later on at a bar she pulled me to the side and told me that she knew something was wrong and if I wasn’t willing to talk to her about it, then she’s making a mistake with me.  I was insulted and we left.  I took a walk after I dropped her at the apartment, when I returned she was extremely apologetic and said she didn’t mean it, she doesn’t know why she does ‘these things.’  She tried to get cuddly but I just wasn’t into it, everything felt cold, and I flew out a few hours later as scheduled.  I like her a lot during the good times, but not during the bad times.  How can I get back the good times?

Not sure that you can. Your good times might be castles built on sand, and unless you are willing to make a strong effort to figure out if they are, this is probably where it ends.

Her actions are nervous and unsure, which is wholly understandable when looking at a relationship that appears to have little long-term potential.  You probably do mutually like each other at some level but you must attend to that budding love properly or your feelings won’t matter.   When things are stable, things are good.  Look at the first three nights back you wily ex-pat.  Honeymoon.  You’re only a pinch and a giggle away.  The last night, before the goodbyes, before the swirling mysteries across seas, you misread each other and fear the worst.  You, she believes you’re having a bad time and won’t say why (should’ve said because “I’m going to miss you,” you manipulative jerk) and responds poorly, she, having realized that she’s probably overly insecure and makes a mea culpa, only finds your prideful cold shoulder. These are the actions of people that don’t have confidence in one another or are self sabotaging a relationship that they, deep down, don’t believe will work.  You must find ways to build confidence and trust and distance can be a large impediment to that.

Another difficulty is that you haven’t known each other very long.   You can’t be sure if are dealing with a person that creates unnecessary drama and she can’t know if she is dealing with someone that makes stink face when he’s having a tough night.  Without the distance you could work and smooth these things out naturally but now you are playing guessing games because you don’t have enough quality time to get to know one another.

This leaves you in a tough spot.  You can’t un-ring the bell that you told her you had deeper feelings for her.  While arguably romantic, you created an unnaturally advanced situation neither of you were prepared for.  Unless you’re ready for a serious rededication that goes well beyond a plane ticket and a lovelorn email, I’m talking RomCom moves, then you probably should call her and let her know you’re sorry you led her on, apologize about the last night and end the relationship.

I’ll move anywhere for you South Florida, serious RomCom moves, just tell me your trials and tribulations at