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Dear Chloe:
I don’t think that it will be difficult for you get him back into your life because he had very pleasant experiences with you, experiences he remembers, and because his relationship with his ex/ current girlfriend has been very unstable.
It is possible that they will stay together and their relationship solidifies, but more often than not, history repeats itself, and it is likely that they will separate yet again. Even if they stay together, he is likely to look for .. more, more romance, more sex, something new, something renewed, and if you let him know that you are interested, you may very well be that something renewed.
Depends of course on what it is that you want with him: an occasional hookup situation or a monogamous, committed long term relationship, or something else. What is it that you want to have with him?
anita