Attracted to my younger guyfriend

Dear Edahn, 

I am attracted to a guy in his late twenties who is also six years younger than I am. As far as I can tell he likes me. I have been out of a relationship for some time though I would not mind going out with him. We talk, but we are not close. How do you think I should go about it? I need some help.

Hm. Does he have a blog? Maybe an advice-related blog? Have you considered leaving a comment on it and asking him what you should do? That's kind of suggestive and flirty. Maybe he'll get the hint. Then again, maybe he won't.

If you already talk and he seems to like you, then what I'd suggest is engaging him a bit more often. You can start by upping your communication by internet (Facebook, email) and then going to phone if he seems to be reciprocating. You want the transition to appear seamless. If you already have a flirtatious relationship, then continue. If you don't, then start teasing him a little by making fun of him in ways that are clever or witty to avoid appearing malicious. You don't have to be a comedian, but a joke here and there is useful.

Within a week or so you can invite him out to somewhere non-threatening  like a bookstore, mall, or vintage clothing shop and play. You can then transition into something a little more sexually charged like a wine bar, pool hall, or maybe some type of club, assuming you can make it seem like it's something you want to do because it's generally fun and not because you want to jump his bones. By the end of the night you'll probably end up hooking up. Doesn't matter who makes the first move as long as you feel the chemistry. Play it cool like it's something that's possibly going to happen again, but if it doesn't, no big deal. If he freaks out and pulls away, let him but keep spending time with him.

Alternatively, you can try just being straightforward and asking him out on a date which you treat, but if you've already been friends for a while during which time you've been single, then taking a more surreptitious route would be your best bet.