How should I respond to this message?

[ashleym]

Long story short, this guy had a huge crush on me in my senior year of high school when he was a junior. He made it obvious, but I always acted stupid when he'd flirt because I wasn't sure I felt that way about him and I had feelings for someone else. And it was also a combination of kind of being afraid of dating because I'd never had a boyfriend then and I still never have. I'm really shy and it's always scared me a little. The guy I really liked ended up with a different girl and I was really upset about it.

On the last day of school the junior texted me, telling me he liked me and that he wanted to take me on a date. I told him I wasn't wanting to date at that time and he said okay. He made a Facebook a few weeks later and friended me. I was scared he was going to try and ask me out again, so I didn't accept his request. I know, it was mean to do, but I wasn't thinking and was really emotional. I've been feeling guilty about it lately and finally accepted it, a year later. I realized how awful it was of me to hurt him by turning him down and then cutting him off like that.

I messaged him a few days later and asked how he was doing. He asked me how college was, so I told him. Then I asked him what his plans are now that he's done with high school. He said "going on a road trip, then settling into college, and as corny as it sounds, searching the long search for "the one."

 

I'm not sure how to respond. Should I just ask him questions back like "where are you going on your road trip?, where are you going to college?" and maybe something like "aw, you're so young. Don't worry so much about finding "the one" yet. You've got plenty of time."

 

I don't know what to say. Should I reply to all the things he said or say something else? Or ask something else?

[DN]

Tell him you were really shy back then but have matured a lot since and would like to ask him out.

[Silverbirch]

^^ Ditto He sounds very nice.

[Pineapplejuice]

Ask him if the road trip is towards you, then he doesn't have to worry about finding the one anymore.

Something like that.

[Helis4life]

I find trying to talk about any more then 2 topics simultaneously through text gets hard to follow. Id stick to 2 and if you run out of things to talk about you can come back to the other topics and keep talking about that. Or you could just call.

[Pineapplejuice]

Or say "(...) we've got plenty of time" .

[F63]

^Exactly that, but put the winky face in the message as well. it's kinky, and I guys love it (or at least I do).