It's a good idea to meet a person first before considering romance. If he is willing to come to your town then sure why not meet and see where it goes. I wouldn't suggest dating until you meet etc also try not to repeat the same mistakes. With last guy you were also the one to ask about texting then meeting etc With this guy you asked if he would date you ( nothing wrong with doing that) but now you want to ask to Skype. Try to do it like give and take. You initiate one thing and he initiates next move. Etc

I did long distance dating once and although the guy was nice the long distance component just wasn't working for us. But I know people who managed it well

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