Honestly, I think you shouldn’t bother with this guy. I mean, the fact that he was 18 and you were a 15-year-old virgin when he slept with you is already borderline shady. There’s just such a big difference between a 15-year-old inexperienced girl and an 18-year-old guy. So, in my book, that’s one strike against him. But the fact that your mom tried to put him in jail and that didn’t scare him off forever — or at least until you are living on your own, totally independent of your mother (and no, paying for your own food, gas, and clothing doesn’t count as totally independent) — is a pretty big second strike. Even if you could overlook the fact that he slept with an under-aged girl — fine, he was just barely legal himself — I think it speaks volumes that he would want to reconnect with you at this point knowing full well how controlling your mother is and that there could be some serious repercussions if she found out you two were seeing each other, if not for him then definitely for you.
And what might those repercussions be? Well, you’d know better than I would. But I’m assuming that your mother, who reminds you all the time that she pays for everything, is footing your tuition and will continue paying for your education as well as maybe your room and board when you transfer to a university this fall. I suspect that, if she’s as controlling and vindictive as you make it sound, she might stop paying for your education. Do you really want to risk that for a guy you were into when you were 15?
If you’re willing to take the risk, I guess I’d just tell your mom now that you’ve recently reconnected with him and want to spend some time together. As for how to tell her without her making your life a living hell, I don’t know. It would seem that, if you wanted to avoid the “living hell” part of the equation, you’d just lie low for five months until you move away and have some distance between yourself and your mom and can have a little more freedom to do what you please. I’d think you would also appreciate the freedom that comes with not being tied down to any one person so that you could fully appreciate all the perks of college life and all the many, many new people you are sure to meet. People your mom didn’t try to jail once upon a time.
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