I am the absolute worst at approaching women, historically bad. I am very social but when it comes to actually talking to a member of the opposite sex, I become shy and shut down. It's mostly because I think, "there's no way she's single, don't be weird," or "she definitely won't be interested in you."

I have tried Tinder and Bumble, but I am not a fan of either because it feels so disconnected from actually getting to know someone. I like meeting people face to face because then you can actually have a conversation and I can find out pretty quickly whether it's a possible match.

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Bozeman is probably one of the toughest towns I have tried to date in, due to the fact that a majority of ladies my age seemingly are in a relationship.

How should I approach this type of situation? I have friends that are super-smooth and don't have any problems with this, but I get anxiety just thinking about it. My sister would probably tell me to stop being such a wimp and go talk to her.

Do you have any helpful advice? Email me at will@townsquaremedia.com