Am I playing with fire when it comes to this guy?

Since you are interested, there seems to be no reason not to give it a chance. Right now, the two of you are only talking about one date.

Take a chance! See how it works.

I would go out with him and have a nice time, no commitments and no need to even speculate, since the relationship will be so new. Just go and enjoy and what will be will be.

You’re interested, he’s interested, go for it and give it a shot.

Don’t bring up the age difference unless you want to push him away.

What is bothering you? The age difference? The distance between you? The fact that you don’t know much about him? That really all you have is drinking together and the fact you like the way each other looks?

And in addition, it seems like you find an aura of inevitability about this that you like. You like the story. It’s romantic.

Finally, you believe you don’t want any kind of serious relationship now. Is there a good reason for this?

I would say you have made no promises. I would say that the coincidences are just coincidences and don’t mean anything. I would say that if you want to explore the possibilities and get to know this guy to see if there is anything between you, then you have to date him.

Perhaps don’t over analyze it, go out on a few dates, what harm can it do. Except maybe make things clearer for you.

My own experience with age differences and distance foretell this not working.

@tedd: Who knows? It may work, and they end up serious. It might not and they go their separate ways. It might not and they end up hating each other . They don’t know till they try it. Who knows what will happen down the road for any one of us?

@jca In my case it did work… for a while. And then it exploded in everyones face for a variety of reasons. The relationship ended almost 2 years ago and it still has a daily effect on my life (and I believe hers) and our other relationships (be they mutual friends or new SO’s).

I guess I’m just burned by it, but I would not attempt a distance relationship ever again, and I would be very turned off by trying something with someone so much out of my age/maturity range.

To follow up on the age difference, you’re 21, are you in school? If you have more than a year left of school, age difference can be hard because you are around similarly aged people, while he is “out in the world”.

But how do you guess he is 30? ‘Cuz he likes Avril Lavigne and old J Lo songs? He could be 26 or 27 and look older, or he could be 35 and look young. I think you need to find out.

@tedd: It works for some, doesn’t work for a lot. Meh, whatever. Only time could tell, and she won’t know unless she tries it.

I was in a long distance relationship once. It was a lot of fun, it seemed like it was going somewhere, then he started acting weird. Long story short, I broke up with him and about 5 months later he told me he was getting married to someone. Hello! That explained it!

After reading @zenvelo‘s post above, I re-read the Q. You are guessing his age? Sister, you need to ask. It’s not like it’s a secret or something.

@zenvelo and @jca I know it’s not a secret.. and I am quite curious.. but at the same time, I feel like he might think that I’m sizing him up as far as eligibility for a relationship. I just don’t want to hash out all of the details to something that likely will not materialize. I might consider asking the “friend of a friend” that knows him.. but again, I don’t want to make it seem like I’m overanalyzing this.. (Although clearly I am.)

To those that said to go for it – what about the distance of the date? I don’t want him to think that driving here will win him a sleepover – because that is not the case. I am always leery of accepting generosity from men, be it in terms of money, time, or both in this case. I may have been a bit.. overly friendly.. last weekend.. but I do not want him to think that a visit would come with any guarantees.

Gotcha. The sleepover bit is simple. Just make it clear on the front end. I met a guy once, and he arranged to drive five hours from another city to spend the weekend. I asked if he needed a hotel recommendation. He arranged to stay at a mutual friend’s place.

My (now) fiance and I met online and chatted via web-cam for six months before meeting in person. He was coming from another country. We met in DC and stayed in separate hotel rooms on his insistence.

Either he will understand or he doesn’t. If the latter, then the message is clear as to his expectations.

Why rule someone out at this stage of the game? Maybe he’s the one. Just date for a while no strings attached and see how it goes. The other questions may be answered along the way.

The age difference probably doesn’t make any difference unless it bothers you.

Take a chance and go out on a date with him. What could it hurt?

Thanks for all of the support – I’m actually surprised at how many people said to go ahead with it! Guess I’ll be going on a date soon:)

Good! Talk, talk, talk. It’s question and answer time.

A Lady that dates and younger man is a cougar but a man that dates a younget lady is a pervert. Or so its said. I partial to older women. and your still so young he might be in a different stage in his life then you are and that could hinder the relationship itself. just something to think about.

@nicole29 I have one rule I live by: You don’t know if you don’t try. I use that for most everything and it works pretty well. Yeah, I get hosed occassionlly but I’ve also found some great things that way.

Thanks for the encouragement – it could not have gone any better than it did! And the answers to the other questions all came out, too.

Thank you for the update. It’s good to hear that it worked out. Sooo, what’s the next step?

@Pied_Pfeffer Well, I think he’s coming back to visit for the long weekend. We’ll see if we continue to hit it off, and go from there. I’m not looking for anything serious, but of course that’s how serious things always happen!

I think you should go on the first date and tell him about your age. That would allow you the chance to really get to know him, and see if it could go anywhere. You may think you’re not looking for a relationship but it doesn’t hurt to try just dating him. And if it’s meant to be, it’ll happen.