Dear Orlando,

I am a 23 year old woman and I work as an assistant at an ad agency. I met an older guy at a networking event last fall and we’ve been hanging out ever since. At first, I was totally into him but after thinking about it and hooking up with him a few times, I decided that I should stop dating him. He’s great and I’m attracted to him, but he’s 45 and in a totally different time in his life. While I toil away as an entry level peon, he works in an executive role, makes a ton of money, and has a house in Brentwood. While I’ve made it clear that I don’t want to date anymore, he still likes to go out and enjoys my company so we go out to dinner a lot and he always pays. I know it’s kind of weird, but I feel like if he’s enjoying himself it doesn’t matter that he’s sort of buying my attention with fancy dinners. He recently invited me to accompany him to the South of France and I’ve never been abroad before so I’m tempted to go. I’m conflicted because  I don’t want him to get the wrong idea. I mean, a trip to France seems like something for honeymooners. But I want to go to France. What should I do?

Yours,
Wannabe World Traveler

Dear Wannabe,

While I’ve always dreamed of having a sugar daddy to take me to France, I’ve watched a few friends go on ’round the world trips with Older Dudes and it always resulted in total awkwardness and semi-co-dependency. I would say going is probably a bad idea. It sounds like this guy still has a thing for you, and you’re just making it worse by continuing to hang out with him. You sound like a smart girl to me, so I’m sure you’ll eventually figure out how to travel the world on your own terms. That saying “there’s no such thing as a free lunch” applies here. While it seems like the trip is free, you don’t know what kind of reciprocation your older gentlemen friend expects. And I’m not just talking about sex here. Unless you want to feel emotionally and socially indebted to this guy, I would tell him “no, thank you.” You have your whole life to travel, so don’t feel like you have to do it all right now. This week’s mantra: free is not always free. Sorry babe.

Lovebubbles,
Orlando