Is he being serious? Or just playing around?

I've been chatting with this Chatango chatroom for a few months, and there's this guy who I flirt with and is flirting back with me. I know it's what got me into trouble a couple years ago, doing this same sort of thing, so I'm pretty damn cautious right now. However, the guy, who plays Magic the Gathering (a card based roleplaying strategy game), threw it out there that there was a tournament in my city he was already thinking of going to. I have told him several times that I'm single, and he's said that he's single and hinted that he is into my type (an older woman with long hair). He's 24 and I'm 32, so he's a good 8-9 years younger than me.

I just don't know what to make of it. Is he being serious? Or just having a flirtatiously good time? We both have had bad experiences with the opposite sex before, and I have openly asked him if he'll date me for real. His response is that the distance between us, seeing as he lives nearly 8 hours away from me, is a huge factor, and he needs to get to know me better, as he doesn't know much about me. He finally said he'd think about it.

That was last weekend, and I decided not to push the issue as I don't want to get into another mess, and I don't want him to be in a relationship he doesn't want to be in. I haven't told him about the last time I tried dating a guy I met on a dating site, or the downfall I went through, mostly because I don't want to freak him out or guilt him.

Maybe I should come clean with that. Either way, what do you think? Is this a budding romance, or purely harmless and meaningless flirting at it's finest?

I think you are jumping the gun, by suggesting you date ,if you haven't yet met IRL.

A lot of couples start off online and then meet IRL later on.

I know. I am saying maybe yo won't like him IRL. So just meet him first.

I would like to meet him. But first, wouldn't it be a good idea to talk on Skype, or video chat on Skype?

Yep. Those are good ideas.

Okay, I'll ask him about Skyping.

It's a good idea to meet a person first before considering romance. If he is willing to come to your town then sure why not meet and see where it goes. I wouldn't suggest dating until you meet etc also try not to repeat the same mistakes. With last guy you were also the one to ask about texting then meeting etc With this guy you asked if he would date you ( nothing wrong with doing that) but now you want to ask to Skype. Try to do it like give and take. You initiate one thing and he initiates next move. Etc

I did long distance dating once and although the guy was nice the long distance component just wasn't working for us. But I know people who managed it well

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I did the waiting thing after asking and offered to share my skype all in one go, and he said "I'll think about it."

Should I ask him if he has come to a decision? Or wait until he does something. Hell, should I say, "It's your move what happens next." or something like that?

Way too much pressure by asking.

Sometimes just letting things take their natural path is best.

Seems like it went from a nice flirtation and his coming to your city for his hobby to,..... omg he's flirting...must..snag...him...and ...get commitment.

LOL, I can see where that can be too much pressure on him. I guess it's been a while since I have been ravaged by a man that I'm thinking of ways to get there again and fast.

How does one cool their jets and lets thing progress naturally without feeling the desperate nagging need of sex right there in their mind?

Well....it's a matter of not putting sex as the number 1 priority in finding a relationship. That's the added benefit.

In my opinion, consider the possibility that he's not serious seriously.

I suppose so. I just want something I shouldn't be focusing on right now. Maybe I need a change of focus.

I've been blessed to have two male perspectives on the topic since my marriage. My marriage likewise shifted my perspective as I learned that it can be the exact opposite of a bonding experience, I'll leave that at that because I'm not up to villifying my marriage at this moment, it's too complex for words.

One friend explained the need for touch as a way to feel connected in life. There was a part of him with a void, a sense of deprived for affection type of void. Emotional deprivation leads to feeling that touch would satiate that. Nice guy, just tough relations with women. Does admit to maternal struggles. Mom and dad didn't act emotionally warm to one another.

My other friend, he also, needs that emotional connection. The bedroom was a hostile place for him in the sense of the women that he had been involved with. Would rather go without than subjecate himself to being devalued. With him, timing was perfectly placed for me. He has shown me how a woman can be amired, feel connected and not a sexual object. What happens when old and fragile if that's no longer an option? What's left is touch. Non sexual touch. If emotional connection is intact, if there's attachment at that level...orgasms are nice, indeed, but after the orgasm is where the relationship exists.

In having an emotional connection, it takes two independent personas to blend together.

Hence all that chatter about focusing on oneselves, ones own interests and letting the relationship come to you.

If you offer next step in a progression and a man says "ill think about it" it is a sign he isn't too interested.

It's ok to initiate things and many shy men do like if a woman initiates things. But you have to watch his reaction.

If reaction is "I am so glad you asked as I was afraid to ask you in case you think it's too soon. Are you free this weekend? Can we meet for coffee this Saturday? What time is good for you?" Or "can I call you tonight we so we can discuss our plans? When are you home from work?" Or in case of long distance "can we talk on the phone/skype/ etc tonight? Saturday night? What time are you free? I can't wait to have a normal conversation. " etc etc

If you initiate things and reaction is he needs to think about it, it's not a good sign. There is nothing to think about. I'd move on.

As about how not to get all involved too soon is make a goal to become good friends first and when that happens then wait for romantic feelings/love and only then have sex. It's ok to date steadily for several months prior to becoming intimate

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You always tell me to "move on". What's with that?

I know people who have gotten to know each other online, it has progressed to romantic interest and has been wildly successful - so I'm not in that camp that thinks that you shouldn't even consider such things until you've met in real life.

That said, I'm not sure I've seen a successful relationship born from this kind of superficial dynamic. i.e. His type is an older woman with long hair. At twenty-four years old, there are about two billion women in the world that are his type. With so many woman to choose from, it certainly would be more convenient to find one closer to home. And frankly, his description of 'type' sound more like hook-up qualities rather than relationship qualities. For instance, my type is my wife. The qualities that made her my type were her kindness and compassion, her love of animals and children - things like this.

I'm not trying to dissuade you in the event that you are looking for something casual but I'd hate to see you get your hopes up for something more serious when he's giving signs he's not.

I don't know what to make of it either based on the information you've been able to provide. It may be that there's a definite answer in there but you missed a key detail - or it might be that know one could know at this point. To be honest, I'm not as put off as others here have been with this response though. Eight hours away is a big number - and while I would have done it for the right person, there would be a lot of 'maybe the right persons' that I'd have passed on because it's just too much effort for a long shot. Meet up if he comes to town and that answer will probably be answered.

Good luck.

Thank you Yagr. You can truly sense my confusion.

Would it be too much pressure in his direction if I pressed him to give me a definitive answer on where all of this is headed? Or would I be acting too needy or too demanding?

Well I only suggest to move on if the guy isn't interested or isn't following through like wouldn't reschedule or call back or doesn't sound seripus. I don't want you to waste your energy on something that doesn't sound promising. I wouldn't advice to move on if something is going well. Like if the guy wants to meet you or wants to talk or you met him and it went well, id never say to move on. I'd suggest you go for it!

I think so. I mean, if it were me - and if I were open to the possibility of this being something I wanted to pursue, I wouldn't know where I even wanted this to be heading until after my tournament and meeting this lovely lady (that would be you). At that point I believe that he would be in a much better position to give himself an answer - and hence give you one.

As you know, meeting in person is totally different from chatting online. Online "dating" is a good way to get to know them, but they can be whoever they want to be, and so can you. I would suggest just keeping it on a friendship level until you meet in person. How would you react if he kept asking you "would you really date me" or appearing needy or pushy?

Why not just meet him without expectations and go from there? You might be wildly attracted to each other or might be repelled. Any good relationship should start with friendship first. Don't expect anything and you won't be disappointed.

I hope you get to meet him and just have a fun time.

You are asking for definiteness when the situation, by its very nature, can't be definite right now.

Eight hours is a very long time to travel. Each way.

It is hard to navigate personal relationships. So many unwritten rules and nuances.

It sort of reminds me of my son with asperger's. He is a teen and will soon have to deal with this.

Have you ever wondered about autism or aspergers?

Don't have that. Went to a therapist to see if I did have it and he said I didn't have it.