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We eventually broke up (more than 2 years of him making me feel like crap because he couldn't get over his ex, and when he finally did, I realized I just wasn't happy anymore feeling like I was going to be second fiddle the rest of my life), but we started out similarly to you and your girlfriend: he had been with one other woman and I was a virgin. The thoughts of him being with her tore me apart. He was the one who brought it up first, and for a while, I was so insecure that I kept asking questions. The answers to those questions made me feel MORE insecure. Finally, I was able to control the urge to get reassurance and stopped bringing her up entirely, but the damage was already done.
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