There is a guy in my college who is quite a bit older than me and has been displaying flirtacious behaviour for a while. Here is my point: While at first, that is the first two years that I knew him I felt nothing at all other than amusement at his jokes. But a few months ago I realised I did feel something for him. I thought it might just be a crush and waited but my feelings for him became gradually stronger and now I feel I'm rather in love.
He is working abroad at the moment and will be back in college at the start of term, so I don't see him around but I miss him.
He has, as it seems to me, become more interested as well but it all was quite vague. He is the generally flirtatious type and as long as I know him (to my best knowledge) he has not been dating anyone else. Also he is 15 years older than me and likes to tease me about my age (you can do the maths yourself). But lately he's been dropping other comments. Like last year when I started dating another guy he said something like 'all the good ones are gone'. And he started this accidental touching thing, at least that's what I think it is. That is when we were walking from somewhere side by side, he would 'accidentally' touch my arm or even my butt(!) but it would be so subtle that I'm not sure myself about it. Last time he was in town for some paper work he came into college and since I had helped him with some research proposal he took me for lunch (yes he paid) and he (we are talking about someone dating somebody older) asked me what my upper age limit was (I gave an answer within his range). You see what I mean, he drops the occasional marriage joke as well and things like that. Of course he makes a lot of eye contact and smiles a lot and so on.
I wonder whether I should make some sort of move? It could be that he's just playing but if he just wanted a flick or a night, he has been pretty patient (two years almost). Maybe he is also not sure whether I'm interested or whether he should really ask a younger girl out.
Please give me some ideas because I'd really like to give this a chance.

Sounds like there might be an interest there... you have a choice either you can wait around and see or you can ask him if he wants to go out and do something.. a movie whatever... he may be too afraid to approach you due to the age difference

Hi OP would like to ask, are you sure he's not married or in a relationship, with either m/f.

If you're sure he's not then I would say go for it. As long as you're not treading on anyone's toes then give it your best shot.

Good Luck.

Thanks for the prompt answers! No he is definitely not in a relationship because he said himself he was single and he's been saying it for a long time (also if he had a girlfriend his flirting with me would be very hurtful to her if she found out) But yes he is definitely single. Not sure whether he is the type who wants to stay a bachelor forever, he is 38 by the way!
I wonder if he is interested in this other girl who goes to college with us. Apart from he also seems to be in more or less regular contact with her but he not flirty to her when he's around. I guess I'm just jealous of any other female contact...
Thanks for your answers though, that helped!

How long has he been working abroad? Did your feelings for him grow 'stronger' long before he went abroad or when he was preparing to leave/after he left?

Are you sure it isn't his absence that is making you feel more for him than you thought you did? It is easy to mistake friendship for love when we miss someone. Yes, a friend can be extremely jealous of another person getting too close to his/her friend. Jealousy doesn't indicate love. It shows insecurities and a need to control a relationship.

A caution: People in relationships can and do flirt. IF you get into a relationship with him, DO NOT expect him to stop flirting with other women just because it might hurt your feelings. You know what he is like. Be sure you can handle it if you do go out with him. Discussing boundaries and setting them together is good, but demanding someone change to suit another's needs is not.

Thanks for the advice. No I felt my feelings grow stronger for him long before he went abroad and I don't regard him as a friend anymore since I have different feelings for him now. But when he left it became clearer to me that I wanted to be with him. I don't see myself as a friend, I think we were never really close friends (maybe because of the age difference) since he probably has had a different interest in me for a long time, so it's not like we shared free-time activities or hobbies together much in the past. We only ever saw each other in college.
I am usually not so much of the jealous type and am happy to leave enough freedom to my partner. I think I'm jealous now because I'm not sure of his feelings for me. I know he wouldn't completely stop flirting with people if we were in a relationship and as long as he means nothing serious by it, I would have absolutely no problem with it because that's the way I've always known him and at that age they usually don't change...

Hi I've had allot of experience with this situation " as a man i may feel that a girl is only being nice if she is being flirty so all i am saying is that you should find out if he likes you if he does then get right in there "all a guy really wants is the girl to make the move believe and trust me on this one :)

If he is just "flirty" and you say you're in love might cause you to really analyze for feelings.

Go slowly, too much too soon can be overwhelming.

Good luck.

Hi joe15,

I appreciate a guy's answer on this. It is always best to get an inside view. I have been thinking about making a move, all right. How though Do I make sure that he likes me and doesn't turn me down once I ask? Also as he is still abroad I will wait until he is back for good so I have a chance to do it in person which I always prefer.
Thanks a lot for the reply though!!

There are no guarantees. He could have met someone while he has been abroad. Talk to him. Be friends with him. Ask him out as a friend. Get to know him someplace other than school.

Good luck.

I've actually known him for a while (since 2007). And we have met (in a group) for hikes and movies outside college or for dinners together. I am suspicious of that other girl but I have no firm ground to base my suspicions on other than that they keep some sort of contact as well. The two of them were recently invited to a wedding of a common friend and he paid for all her food while they were over (she is unemployed, he is working fulltime currently). I am in doubt that anything serious is going on between the two of them. I think I'm afraid that he might prefer her to me since she is older and has hence more life experience, but I could be completely wrong. Obviously I can ask neither her nor him directly if they're dating but he is flirting with me to an extent that I would find annoying if I were his girlfriend (see examples mentioned above). I guess I have to be patient and wait until he is back. She also wants to be back in college from next year on but might not be able to afford it. It might just be that they have more in common as friends since they share similar life experiences (they are still nine years between them as well). Unfortunately I am not a very patient person; right now I'd simply like to know whether he is seriously interested in me and I wouldn't have the courage to just ring him up to pop the question directly.
Thanks for all advice!!

Hi and its my pleasure to help you out" when a guy likes a girl take me for instance he will be so shy about it "guys allways want a miracle to happen where the girl will jump into his arms and everything will be great but we both know that will not happen :) what I would suggest is to get to know him very well if you have his number message him "when you are messaging him be sure to throw in a few flirty signs "believe me if he is anyway possibly into you he will love this "GOOD LUCK :)

hi and its my pleasure to help you out" when a guy likes a girl take me for instance he will be so shy about it "guys always want a miracle to happen where the girl will jump into his arms and everything will be great but we both know that will not happen :) what i would suggest is to get to know him very well if you have his number message him "when you are messaging him be sure to throw in a few flirty signs "believe me if he is anyway possibly into you he will love this "GOOD LUCK :)

This is a 38 year old man. He may be past all of that.

I think this is a 38 year old man who likes young women and flirts with them.
If he was serious about you and he has been doing this for some time I think you would know by now.
I would hate to see you get hurt. How is it it you think you love him, other than flirting what kind of contact have the two of you had with each other?

Well he is a very mature guy and very busy at work. I don't know how much he would appreciate if I just rang him up to flirt. It's hard to know how to make contact with him. He might find it childish. I thought you guys (espacially the more mature ones) loved pursuing the girl and girls who are harder to get. But I will ask him out if he doesn't make a move once he is back.

Well he is a very mature guy and very busy at work. I don't know how much he would appreciate if I just rang him up to flirt. It's hard to know how to make contact with him. He might find it childish. I thought you guys (espacially the more mature ones) loved pursuing the girl and girls who are harder to get. But I will ask him out if he doesn't make a move once he is back.

Just to put Joe's 'experienced' advice in perspective, he is 15 according to another post in another thread..

I know it is difficult to stay patient and wait until he gets back, but there really isn't anything else you can do. This isn't a subject that is easily handled over emails or texts. There is way too much chance of misunderstandings occurring.

Don't let waiting keep you from enjoying yourself and your friends. Keep yourself busy and the time will pass by much more quickly.

I'll ask again, how is it you think you love him? Other than flirting what kind of contact or interaction have the two of you had with each other?

Sounds to me like this is pretty one-sided but you can ask him out for a coffee when he gets back. Have a one on one talk with each other. Maybe you'll get a better idea as to how he feels about you.

Well, if I say 'I love him' it makes it sound almost epic! I have quite strong feelings for him at this stage. We have not gone out just the two of us alone since I was in a relationship myself until this year. I would like to go out with him and find out how much he feels but he has been pretty bold with flirting. The other night we were talking on the phone because I needed his advice for some forms to be filled in, so we were also just small talking about what's new and he said he was a boring husband because he had no news. See the type of 'joke' he was making. I have experienced guys doing that when they want to know whow far they can go until the girl tells them to f*** off. So he's been making jokes of this kind a lot. So I need to confront him about that soon I guess and I will once I get a chance, and that is in person and in person only.
Thanks for all the advice!!

I only have one more caution for you: Have you truly healed and moved on from your last relationship? Take some time to be certain that you aren't 'falling' for this gentleman because he is available and seems willing. I don't think you want this to turn out to be a 'rebound' situation.

Good luck. :)

I don't see that as flirting, it was a joke, one I did't get. But anyway, you'll have to just go out with him talk to him and get a better idea of where is head is.

@ cat1864: It's not a rebound relationship. I didn't want to mention that here but I left my previous boyfriend since I had feelings for this guy and they were not getting weaker. I had to break up with him. But that's another issue and yes I'm over the last relationship.
At homegirl50, OK it was out of context for you. I just wanted to give an example of the kind of remarks he drops now and then.

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.

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)?

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.

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?
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.

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.
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...