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I’ve currently been talking to a guy who’s 20 yrs old. I’m turning 24 in a few days. 
We met at a get together in January and it started off as pretty clear that we were both still emotional unavailable. He was smitten with me and was very nervous to even talk to me. I felt like a cougar. He started texting me every day and wishing me good morning. I made it clear that we could only be platonic friends. But then we started getting close. Cuddling, kissing and eventually intercourse. He grew on me. 
Our first time was pretty bad because he’s only had 2 partners. I’ve had far more. I may have been too honest about my lack of satisfaction. We didn’t talk for 4 days after that and then I had to make the first steps to contact him. He was too embarrassed, we cleared it up in the end. 

So it lead to this: He says he’s afraid to get hurt and attached to me. That he doesn’t want to start anything, that sex makes him feel used and weird. He wants to stay friends but when we are together he gives me puppy eyes and is really nice to me. He worries about me if I say I’m sad and lets me vent. Kissing just always happens. He asks me if I’m seeing anyone, what I’m doing. We always talk. He’s coming over to mine on Monday for my birthday. First time we’re gonna hang alone since that night. 
I told him I don’t want to rush and I am only ready for casual stuff right now. We tell each other anything. 
WHAT IS HAPPENING? Am I wasting my time???
Dear What’s Happening,
There are four things going on here:
1. You like each other. This is clear. Perhaps it wasn’t love at first sight, but you seem to like being around each other and enjoy each other’s company.
2. He’s very young. Both in age and in relationship/sexual experience.
3. You are very young too. Perhaps you’re more experienced sexually, but going from “Hey, we’re platonic. Nothing is happening here” to “Ok, you can put the tip in” in less than a month is a sign of someone who might think they know what they want, but really don’t.
4. He likes you more than you like him.
Fortunately, none of these are bad things. What can potentially be a bad thing, though, is if you continue this ambiguity without any type of parameters or rules. Casual with occasional sex works in theory, but once feelings are involved — and, again, you both seem to like each other — “casual” has a tendency to lead to “hurt feelings.”
Basically, if you want to date each other, date each other. And, if you want to just be cool with each other and leave the sex alone, just be cool with each other and leave the sex alone. Either way, figure out what you want, have an actual conversation about it, and…follow through. Only then will you be able to gauge whether you’re wasting your time.
Sincerely,
Damon Young
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