How do I get back into the dating world?

So first, a little background information. I’m 21 and have been single for three months. Before that, I was dating someone for 4 years (approx. 16-20). He was also my first boyfriend.

I do like someone now, but I find it hard to read him. He’s outgoing, but I don’t believe he’s much of a flirt. We’ve been friends for over a year and there are times when I think he likes me, but I am not always sure.

For instance, he gives me two-armed hugs instead of the one-armed side hugs that he gives most girls. He has a tendency to hold on longer and sing a random, ridiculous song while doing so. He is also more cautious with me, making sure that he hasn’t offended me with something he said, but everyone is like that with me, so it could be nothing.

He teases me, especially when I do something to deserve it, such as poor word choice. Another time was when he was giving me a hug and was tipping my chair over. I told him that I didn’t want to fall. He tells me he won’t let me and then proceeds to pretend like he is actually going to drop me. Also, occasionally he uses my full name if he specifically wants my attention, such as when he wants to see my reaction.

One time, I was sitting next to him once and wearing a belt with fringes. He took my hand, put it in the middle of them and tied my hand into it. He also tied objects on it. That same night, he was pawing at my hand, but I was leaning back on it, so I didn't do anything.

I also wear hats a lot, so he occasionally takes and wears them. I let him do this, as I trust him with my things. When I went to my school’s formal event, I was wearing a hat with my dress. He was one of the first people I saw. He didn’t say a word, but came up to me, ran a finger down the brim of my hat (the part in front) until it dropped off the edge and then tapped me on the nose. Then he just smiled at me and walked off.

We’ve had lunch together with just the two of us. Otherwise, I join his group. When it’s just us though, he tends to be a bit more serious. The conversation is still fun, but not as random or crazy as with a group. What makes me wonder on this is that his friends will be sitting twenty feet away, and yet he’s with me instead. I’m a quiet person, so I don’t talk much unless someone comes to me first.

I thought some of these were just my friend being himself, as he loves to make people feel awkward. However, if he truly wanted it to be awkward, he would ask if it was, hoping you’d say ‘yes’. He’s asked me before, but not for any of the incidents mentioned.

College has been out since May, so I was only single for two months of the semester. I wouldn’t be surprised if he (or any boy) didn’t say anything because of the time and distance of summer. I’m not too shy to tell him that I like him, but I promised myself that I would not. I spent the last 4 years of seeing all guys as only friends and being oblivious of flirting. I would just like to know that I’m not reading too much into this.


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Most Helpful Girl

  • It's hard to say without knowing the guy, but it definitely does sound like he likes you, especially since you said he treats you differently than other girls. I think teasing is definitely a sign of a guy liking you. The hugs thing would make me wonder, too.

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