From "one nighter" to "FWB" to what next?

I went to a concert with my friend and he decided to invite his other friend whom I didn't know at the time. Night was young and I didn't want to go home so we all decided to go back to his friend's house. My friend passed out and me and his friend stayed up talking. Me and the friend ended up hooking up that night. A few days later, we hooked up again. Long story short, we have been at this texting back and forth hooking up thing for a couple of months now. I see him usually twice a week and we text at least every other day. Every time I go over there, we talk about stuff from religion to babies to work, anything and everything, for hours before the deed ever gets done. Sometimes the deed doesn't get done. He harbors a lot of resentment for his 2 exes, one left him for a girl and who knows what happened with the other. He has told me that he knows he has a heart and it is obvious that the wants to be with someone and he wants to start a family but his job puts him outta town a lot for weeks, sometimes months and that would make it hard. His ex (the first one) has been writing him letters recently talking about how she regrets what she did. He told me that he doesn't know what to think about it, and told me he knows that I don't want to hear about this. I said not really and he hasn't said a word about either of them since. I told him that I kinda liked him but he really didn't have a reaction at the time (this was a month into it) but texted me later saying he couldn't help what he felt. Thing is, we decided to keep our thing going. I'm at a crossroad, because the more we hang out, the more he divulges to me about his life and the more into me he seems to be. As far as the deed goes, he has made it clear that he wants kids and he knows that I am not on BC and hasn't pushed me to get on it even though I have brought up the BC subject a couple of times. Did I bring up the "I kind like you" thing too soon or is this one of those things that takes more time to develop given his past relationship experiences? I'm cool with FWB thing, I'm just kinda wondering where this may lead. I don't want to bring up the I like you thing again until I know more I guess. Unbiased opinions would be nice...

Updates:
He's a jerk...decided to work things out with the ex

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What Guys Said 1

  • "Thing is, we decided to keep our thing going. I'm at a crossroad, because the more we hang out, the more he divulges to me about his life and the more into me he seems to be."

    He is "off-loading" his unhealed wounds. People do that with their therapists in "talking therapy". It works for some people, re-living their unwanted memories and bringing a closure to them. Some people don't; they are the ones who use this technique to draw attention/care to them, and develop an addiction out of it. This kind is manipulative; they manipulate others using their past wounds, and suck others' energy out.

    If he keeps repeating his stories like a broken record, having no intention of healing himself except moaning in eternity, you must put a stop to that. What you hope for, of course, is upon his dumping out his junks he gets healed and develop a healthy relationship with you.

    Ask him, after he finishes one such off-loading "session" with you, is "Now that you have off-loaded those wounds, what are you going to do next?" This brings him to the awareness of what he is doing with you, and at the same time tell him you know what he is doing. It also puts him on the track of bringing a closure to the past, and step into a future with no more emotional baggages.

    The one thing I am slightly worried about is that he said he knew he isn't supposed to do that, but he can't control himself; evidenced by his doing that. Tell him his happiness is HIS responsibility; not his parents', not his friends', not yours. If things get out of hand, tell him he should be doing this kind of off-loading with a professional therapist, playing the role of a good listener you are willing to do, BUT you are NOT professionally trained to handle "gabbage memories", and their source, namely him.

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