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Should I Make the Next Move?

"How Do I Approach Him Without Being Too Forward?"

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

I've asked for advice in this forum before, they all go into details about my behavior with boys and my own inner over-analyzing battle. I've gotten plenty of advice like, "just stop being so desperate" or "your problem is just that you're too impulsive and too eager." I get it; it's just a nice way to say that I am being easy, that I don't act as if I'm worthy of being wooed and that boys just don't make the effort because I've acted like they don't need to.

I'm not going to say you're all wrong because you're not. Although I’m not going to sit here and take all the blame and not acknowledge that some of the guys I've dated have been real jerks, I'm also not going to say that I'm not liable for my failures.


I know this is a long process, one that needs a lot of self-evaluation and self-appreciation. It is something that I've tried to improve and better myself at, but now I'm genuinely afraid.

I've met a guy. When we first met at the bar he was charming and engaging — he asked me for my number in one of the sweetest ways possible and though the situation was completely sabotaged by my friend, I was still pleased on how the night went. He texted 3 days later, exactly a week ago, just to chat; this unfortunately means that he didn't ask me out at any point of the conversation and that he hasn't texted me ever since. I would usually be a bit more forward either by texting him now or suggesting we meet again soon, heck we haven't even met so I most certainly have nothing to lose. Now I'm just worried, I don't want to keep being shut down again and again because of being too forward, but I certainly do not want to miss an opportunity, after all he did ask for my number and followed that with a 3 hour conversation via text message.

I'm very aware that he is not and doesn't have to be my 'only chance' to make it right and I also know that I do not know him at all so at this point I shouldn't be so extreme as to over-analyzing a text message, but I feel like tiny bits of rejection here and there is what has gotten me to evaluate my approach to men, also adding that insecurities have built up because being the one making the invitations leaves me room to wonder whether or not the guy wanted the date as much I did.

Like I said, I know that confidence is not built overnight and that it takes time and I'm making the effort to better myself, but I do not want to miss this chance, if this even is one, because I have now gone in full self-protection mode. I guess my question here is — should I text him now after a week of disappearance? Should I ask him out if he doesn't do so in his replies? How long should I wait before texting him again? Or should I just ignore this whole thing because he hasn't looked for me after that conversation last week? Sorry for the overload of explanation to a simple question. I just wanted you to understand why it's been a struggle to make the even simplest decision in this case.

Have a dilemma of your own? Post it anonymously in Group Therapy for advice, and check out what else is happening in the TrèsSugar Community.

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