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And another problem I forsee. She's already dated and come back. Perhaps in her mind she's like YAY I picked him, it's all good... but it may really really suck for her to find out you want your rite of passage too. (or whatever you'd like to call this extra date). Who knows how she'll react but she may be totally thinking you sooo don't need this little extra on the side date.
This is why my dilemma. I do not want to hurt her, but also do not want to "hurt" my self - by may be missing someone good.