Maybe you're not picking up what he's putting down, and maybe he's not picking up what you aren't saying.

That is called playing games. And I don't mean that in a bad way. Neither of you are clear on the intent of the other.

What might make you feel more at ease, and maybe clear up some questions about him that you have is, why not sign him up on your Facebook, or MSN if you have it. Sort of an arm's length way of communicating more with him, without taking too big a step. You can see and learn more about him as well.

Also good for a historical perspective too. Has he been married, does he have children- maybe he is married, who knows. Where does he come from, and why is he in school at his age. What are his future plans, goals etc. Anything really, to add to what little you know.

I think if you knew him better, you would be able to better judge his jokes, comments, etc.

Because you have strong feelings for him, I too, would be holding back, at least until I knew more about him.

If it gets right down to it, and you do want to know him better, then change the game, and add a few more blocks to the pile. Ask him out for coffee. Then just talk to him as a friend would. If the two of you click, and he is somewhere in the same ballpark with being interested in you, a five minute chat will turn into hours before you know it.

I guess the bottom line is, is he worth pursuing? You may wait too long, and never find out, if you don't take a chance and be the one pushing the envelope a little.

Hi!

Thanks for your comment. NO, he is not married. He does not have any children. 100% sure, he is also not in a relationship as he keeps saying he is single. We already are friends on Facebook. He took a career break from engineering a few years ago as the economy was still really strong, then it went down and he couldn't go back to working full-tim since there was hardly any work. He has been pursuing a postgraduate career since and since there are no full-time jobs readily available he'll stay in college until he gets a job again and his supervisors know this. He also recently won a scholarship which is better than being unemployed, being in college. I think I know him quite well already just not in the respect of relationships. I will make a move if he doesn't. Yes, you are right, maybe I should have picked up on his jokes more and made some myself and he would have gone further. But I held back to see if he's not just playing. I think you might be right that neither of us is clear what the other wants. I don't think he expects me to have these feelings for him, if he knew he might have made a stronger move already. I thought smiling and being very nice to him might be enough but I think I have to be more plain with him.

I think it is a good thing he hasn't made a 'stronger play' yet. It has given you more time to truly think about what you want and not just slide from one relationship into another.

Your curiosity is running rampant, and your hopes are very high, and quiting your old boyfriend for strong feelings for another is a good idea, but a serious step. I don't think he is as interested as you are, and if you do ask him out, I doubt he says NO. What single guy would? But if after all this time and flirting and all that superficial stuff its telling that he isn't interested enough to ask YOU out. That's where you pay attention a lot closer and not just get carried away by YOUR own attraction.

Ever ask yourself why a 38 year old outgoing, attractive guy is single?? Answer that question before you get in deeper than you are already. You may learn something you need to know to make a good decision as to what action you should take next.

I have asked myself that question in fact (why he is single) and have wondered whether he is not just a player. But I have only broken up with my last boyfriend while this guy was already away working abroad and since I think he isn't sure either about me or what I want or think, then this could be a reason he has not asked me out yet; there was simply not enough personal contact to do it. But as always, how will I know if I don't at least give it a chance and believe me I'm not walking blindly into this; I have no intention of rushing it once we do go out. But if he were 'not that into me' why would he have been trying for over a year (and I always rejected his jokes and flirts and advances so far, so up until now he would have gotten a no from me had he asked me out and I think he knew that)? If he just wanted a girl he could have been dating someone else in the meantime but it's almost like he's been waiting. I'll see what happens.

I hope you will keep us posted as to how this turns out for you. If nothing else it will give you confidence to know that you can take charge, and call your own shots, without waiting for anybody else to do it.

If you happen to know when his birthday is, why not make him a picnic lunch, and meet him in a public park, and have a cupcake with a candle in it. I really, really want to say, how are you going to fit 38 candles on a cupcake, but I won't go there... (pardon my sense of humour).

In other words, just keep it simple, you have absolutely nothing to lose.

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Originally Posted by Ardae

But if he were 'not that into me' why would he have been trying for over a year (and I always rejected his jokes and flirts and advances so far, so up until now he would have gotten a no from me had he asked me out and I think he knew that)?

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This brings back up an important question: You've been asking why would he flirt with you if he were unavailable. Flip that question around a little bit, why would he be flirting (trying to get) with someone in what he (at least) thinks is a serious relationship? If he is willing to pursue a person who is unavailable, how willing is he to pursue more than one person at a time or even while he is involved with someone? (I am not saying he currently is involved with anyone, only that his values may be a bit questionable when he is.)

I am glad you are keeping your mind and options open. I know it seems like we are nit picking, but I don't think anyone wants you to come back upset because you missed a red flag. Especially, if we can point it out.

Personally I think the guy is a flirt. He is not some young college kid and he has been flirting with you for a year or so, knowing you were in a relationship. He may just like the game.
I hope for your sake I'm wrong. So invite him out for coffee and see how it goes.

I saw your points, all of them really.
I was in the last relation for eight months and he knew my ex-boyfriend, as an acquaintance. Sometimes I think he kept flirting because I let him. I never told him to shut up or seriously asked to stop it. Because I have to admit it didn't bother me too much... so I guess it might have encouraged him to keep going. To address the age. Yes he is 38 and single as long as I have known him (at least he was not in a longer relationship for the past two and half years). He started flirty/teasing behaviour about one and a half year's ago and when I entered my last relationship he said that 'all the best ones are gone' or something like that. A few months ago we had a conversation about dating people who are older than you and I said I wouldn't mind a big age difference (I was speaking generally, not specifically), and he replied in a joking way and nudged me "So there is a chance for us then". I didn't reply to that but didn't criticize him either. He really is a big flirter, but why put so much effort into one girl if, I'm sure, he could have tried all that on other girls and it would have worked for him so much sooner and easier even if he just wanted sex or play games? I thought that more mature guys (than my own age) only keep pursuing when they're interested in something more serious and when maybe they have reached an age where there can hear they're own clock ticking (don't get me wrong I'm not talking about marriage), I'm simply saying that they're beyond the age of mind games and using women. The question why he is single remains in the air though and I can't answer that. I have so far not really confided myself in anyone; I don't want anyone to judge before anything happens at all. Maybe I should confide myself in a guy friend though since he'll understand the guy's perspective better, I guess. I generally like more mature guys, I think. They simply know where they stand in life (mostly) and are more secure than guys my age who have nothing else to do than get drunk (the majority unfortunately).
Also: Patience is clearly not one of my virtues which might make me look like a desperate teenager but I'm like this in all areas of life, I'm afraid.
Thanks again for all your comments. I'm glad I get different perspectives on this.

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He really is a big flirter, but why put so much effort into one girl if, I'm sure, he could have tried all that on other girls and it would have worked for him so much sooner and easier even if he just wanted sex or play games?

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Just because you don't know what he does, or has done when he is out of your site, off campus, doesn't mean he hasn't gotten a few females this way. Casually or otherwise. You are assuming, and that's never a fact until proven.

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I thought that more mature guys (than my own age) only keep pursuing when they're interested in something more serious and when maybe they have reached an age where there can hear they're own clock ticking (don't get me wrong I'm not talking about marriage), I'm simply saying that they're beyond the age of mind games and using women.

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Another assumption on your part, and has no real basis in fact in this situation.

You don't really have a lot of facts here, except he is 38, single, and a big flirt. I strongly suggest you examine your own feelings before you examine his, for your own sake. You need more solid facts.

I think you have a crush on this guy and a lot of wishful thinking. He probably flirts with a lot of women and goes out with a few of them. You have not discouraged him so he continues.
If he was serious about you, I would imagine he would have let you know.

I suppose you have a point. He didn't get a chance to be that serious so far though as I said, I was in a relationship until a few months ago and then he left. No opportunity for serious appraches I guess and before that I rejected his advances.
I won't run into this but I will confront him about either making a move once he's back or quitting the flirting!

Just curious to know if you are in touch with him, while he is gone, via Facebook for example?

I see no harm in messaging him to see how he's doing.

Also very curious to see what a 'normal' conversation would be like for you with this guy.

Most people I know that are funny and flirty, often mask a very serious side too, and are people of more substance than you might think.

Please keep us posted with how this works for you.

Yes he has a very serious side when he wants to show off his maturity and you can have very serious conversations with him about everything. Yes we are in regular contact, phone, email or chat. He's sent me a message this morning and was on chat yesterday although he says he never uses the chat function.
I'll let you know of any further development!

Update: He was over for two days. I didn't really get to talk to him alone but on the last day we had coffee together and he flirted as usual, then he had to leave for his plane. He gave me a hug and left.
I went back and asked him if he would like to go out sometime.
He immediately understood what was meant and first only opened and closed his mouth without saying anything; he then said that this was totally surprising. And I could see it in his face. So I told him to think about it and he left.
He is due back for good in two weeks time. He hasn't contacted me since I asked him which was Thursday.

I don't know what to think but I am not a patient person. I take it that now he definitely knows that I am interested.

I hope he does not withdraw now...