What If You Don't Have Much in Common?

Dear Bro Jo,

First of all, I'm a huge fan of your blog. I think you make some really good points, which is why I'm asking for advice...

I've had some really bad experiences with guys in the past. I've been through the whole child abuse scenario and was sexually harassed by a lot of different boys in high school, so I've become super cautious with the whole dating scene.

Not that I haven't dated at all, I've had a few different boyfriends, but because I'm so cautious, I make sure they complete this sort of list I have.

So most of the guys I've developed any sort of relationship with have been perfect on paper, but I haven't really connected or fell in love with them.

I'm 20 and know it's time I start learning to open up and trust so that way I can get going on the next phase of life sometime soon.

Now there's a new guy who on paper is not a good match for me at all. We have pretty different interests and some of our opinions are really different.

Plus he fails at the whole dating thing.

His friends tell me he just doesn't date much, but is more of a flirt.

We've gotten to be really good friends and spend a lot of time together. He'll plan things that I consider a hang out, and then he ends up paying so I'm confused, realizing he considers it a date.

He breaks some of your rules too- like he texts me a lot.

But he's really different than the perfect guys I've dated.

He has been flirting with me all semester and has always been very observant of me and can always tell what I'm thinking or feeling.

I'm an awkward person by nature, and he thinks it's adorable, which is such a rare thing. He can tell that I get uncomfortable dating, so he plans group things and doesn't push anything, but now I want him to.

It's just he's the first person I've really felt connected with. It scares me how much I actually like him.

He doesn't spend time with other girls and I've never seen him flirt with anyone else- so is he just leading me on or are his friends wrong about him?

How much leeway am I allowed to give him?

Or how to I discreetly tell him to be a man? 

Sincerely,

- Cautious




Dear Cautious,

Everything you've told me you need to tell him; every question you've asked me you need to ask him.

A good relationship does not require that both people agree on everything or that either person conform to some mythical list of required attributes.

Go talk to him.

- Bro Jo