This person is finding it hard to talk to their friend.

Hello,

Sometimes, as much as we may try, some people just don't mesh well. It's frustrating when you're really trying to make it work, but ultimately you can't force something that just isn't there. Sure, the history is there and the desire to reach and maintain a friendship, but if the vibes are off, then there's not much you can really do. That doesn't mean you should stop talking to him. If you want to be friends then, by all means, keep talking to him, but don't expect him to behave the same way as the rest of your friends or the same way he did when you were friends before. People do change over time, so the person you knew him as in elementary school probably isn't the same person he is now. That's not necessarily a bad thing, but it is unfair to expect him to have stayed exactly the same after not seeing each other for a while.

So what to do. Honestly, dear, there isn't much to do here. It sounds like one of the biggest roadblocks in your conversations is that you're not very comfortable talking to him. Not that he makes you uncomfortable exactly, but that you don't know how to talk to each other. You want to talk to him like you do with your other friends, but the energy isn't right. He doesn't respond well to your humor, and the conversations feel dry. You've been struggling with this for five months with little progress, and it sounds like part of the problem is that you're not being yourself (or neither of you is). In order to break past that roadblock, you need to be comfortable being yourself when talking to him. Not trying to force a dynamic you have with other people, and not being polite. Just be yourself. In your conversations, talk about things you're interested in as well. Don't let him dominate the conversation. You're allowed to lead it as well. So tell him about things you like, talk about yourself if you want to, and then let him respond or ask him a question. That way, you won't spend the entire time bored because he's just talking about himself, you'll be engaged because you're talking about your interests as well as his, and over time the conversation will become more comfortable for both of you and you'll find a dynamic that fits your relationship. The more you talk, the more you'll better understand and respond to each other's humor and conversation/text styles.

I hope this helps, love. Good luck, and have fun!

Best,

The Advice Column Team