Would like a fling with this guy, but don't know how to go about it

[Intrepidcaribou]

I'm a 28 year old civil servant. I'm slim (size 4ish), I dress well, I'm sociable and I make good money. The thing is I'm a virgin and I've never had a boyfriend at all and nobody except my family knows about it. I went on a few dates with guys I wasn't attracted to when I was younger -- but nothing that went anywhere. I've decided I prefer to live a full life with art, travel and adventure where I can pretty much avoid housework and cooking -- which means not having a boyfriend. It has made me reasonably content and financially successful. I like chaos. Order and neatness makes me anxious. I'm not interested in marriage or dating. He's not domestic either.

 

I met this guy I find really attractive. He's had an interesting life, is 12 years older than me, but also much more experienced. Like me, he has a job where he moves around a lot. He's divorced, no kids. Very handsome, and very smart. I've never felt a strong desire to sleep with any man I know until I met him. We flirt a lot. We ramble on about the trips we're still planning on taking (me: Paris Catacombs, Antarctica, him: Mongolia, Ellesmere Island). He touches me on the hand or shoulder and I enjoy it. What should I do?

Edited December 3, 2014 by Intrepidcaribou

[Standard-Fare]

How do you know him? And in what type of circumstances are you interacting with him?

 

The same advice would apply regardless of your experience level: Try to flirt with him more to determine if that attraction is mutual. Make eye contact, make light physical contact (like he's done with you, touching on the shoulder etc.), tease him a little. Make it clear that you're interested and see how he responds.

 

If you're bold enough, you could invite him to do something with you one-on-one... maybe not something that's explicitly a "date," but something getting close to that where it's just you two getting to know each other more.

[Intrepidcaribou]

We're neighbours with mutual friends. We live in small and remote but cosmopolitan community where there is a lot of turnover of people. We met having drinks at a neighbour couple's house. I'm friends with the girlfriend. He's friends with the boyfriend.

[Standard-Fare]

We're neighbours with mutual friends. We live in small community where there is a lot of turnover of people. We met having drinks at a neighbour couple's house. I'm friends with the girlfriend. He's friends with the boyfriend.

 

If you know there's going to be a lot of opportunities for you two to continue interacting, you should probably see how things develop naturally, and, as I said, continue with the flirting/affection.

 

But if you think you won't be seeing a lot of him in the future, you'd probably need to take the risk to "put yourself out there." One option for that, given your circumstances, would be to talk to your girlfriend about this guy in the hopes that she'll help set you two up.