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Should I Go on Vacation With My Ex-Boyfriend?

"Should I Go on Vacation With My Ex-Boyfriend?"

This question is from a Group Therapy post in our TrèsSugar Community. Add your advice in the comments!

I am 28-year-old single woman with a great job, great condo and lots of good friends in a city I've been living in for about four years; I would consider myself very independent and self-sufficient. Four years ago I broke up with my college boyfriend — of four years — because he moved five hours away. The pressure I was getting from him caused me to fall out of love and I started becoming interested in other men, which is when I knew I had to break it off. The breakup was very difficult on him and we didn't speak for three years. 

Just this past December we went to dinner and I realized that he had changed; he was confident, well-spoken and apologized for blaming me for "ruining his life." He told me then that he was finally over me.


Over the past six months we have been talking a lot, seen each other twice, and slept together. When we were together it was great and stress free, which it hadn't been before. Since he lives far away, I've been wanting to spend longer periods of time with him so I invited him to my parents' house at the beach. I am very excited, but also very nervous. 

I'm afraid and in the back of my head a voice is telling me that if it didn't work the first time, why would it this time? Also, I still harbor guilt over the first break up, so I'm nervous to let myself go and just roll with it. I'm wondering if there is anyone who has been in a similar situation and knows how to tell the little voices in your head to stop and just have fun. Do you have any advice?

Nervous Nellie

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Join The Conversation
testadura67 testadura67 5 years
I think a lot of time has passed since your break up, so what you really need to assess is what went wrong the first time, and what has changed since then. If the issues that led to your original break up are still around, there's no point in setting each other up for more hurt. If those issues have been resolved and you feel like you two have a real shot at making it work, go for it. However, I think trying to casually date someone you were previously with for several years will lead to heartache for at least one of you. Anyone who says "I'm finally over you", then sleeps with you, isn't being entirely honest with themselves. 
henna-red henna-red 5 years
I agree that listening to that little voice is veeeeeeerrryy important! And it's not just instinct, it's the voice of past experience. The only thing that will lay a previous poor experience to rest, is a whole lot of current great experience. Believe the actions, believe the behaviors, if they match the words, you're golden. Be happy, hope for the best, but be cautious. His past behavior has taught you that. His current apology has taught you to hope. But be very careful to be sure those great words will continue to line up with great actions. Sometimes people learn what to say and not say before they learn to back those words up with right actions. So never, ever discount that little's a voice of wisdom working to keep you safe. good luck with your weekend
plmnko plmnko 5 years
That little voice in your head is there for a reason. If something is telling you this is a bad idea then it is. If you have to force yourself to supress that voice then you're doing something wrong. Trust your instincts.
pixigirl31 pixigirl31 5 years
I totally understand where you are coming from, but I should be more detailed. 1. He's been to my parents house many times before and it's at the beach so there's lots of cool things to do.. 2. We have continued to talk daily for the last 5 months. 3. I'm not looking at this as "confining myself", because we will be in separate rooms and I enjoy his company that I'm not worried that I will feel suffocated here. I don't want to make the same mistake twice, which is why I'm not setting any expectations for this, but how can I just go with the flow to see what comes of this, if anything at all?
BiWife BiWife 5 years
what made you think that confining yourself with an ex that you have only seen a handful of times in over 3 years was a good idea? There's "spending more time" with someone, and there's asking for trouble. If you guys were travelling separately, had separate lodging, and if things turned bad you could just stay in your separate places, then that'd be one thing. But you're talking about staying in the same house with him - same bed? - when you're just barely beginning to rebuild a relationship (which sounds more like a friendship than a romantic thing, unless there's more you aren't telling us). I would call off the trip asap, say your parents' house has a plumbing issue or your folks decided to use it instead, or something if you have to give a cover story (though, I believe being direct and honest is a better option). Let him know that you'd like to do more things together, just not an overnight trip right now. Exes are usually exes for a reason - you don't need to learn the same lesson making the same mistake twice, do you?
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