I'd really appreciate your insight from a man's perspective on my situation.

Ok, here's the background:

1. He's a colleague at work

2. He always beams at me whenever he sees me

Happy to see you, that's very positive.  He only has to look at you to smile, never mind talk to you.

3. We began exchanging friendly and sometimes slightly flirtatious emails.

4. He made me a cd of music and left it on my desk.

5. He asked me if I'd like to go on a bike trip (day out) with some of his friends that might happen in May or June.

6. We exchanged subtly flirtatious emails.

7. I said that I owed him a drink for having done the cd.

8. He immediately suggested a day.

9. We went for a drink, he was really open, we talked for ages about all sorts, he said he hadn't talked about much of what we discussed for a long time, that he felt comfortable with me, and there was some very subtle flattery from his side. He even discussed some slightly contentious issues such as the fact he wouldn't live with someone before he married.

Laying down his cards, and saying to you, so you will have to deal with that, if you fancy me.  So are you still interested in me, after I said that.  The guy wants a dedicated woman, that will accept him, not a half-hearted woman.

The table wasn't exactly conducive to closeness, but by the end of the evening we were almost sitting in front of the table, much closer.

Very, very positive. 

10. He seemed concerned that I would think he was boring and that I wouldn't want to go out with him again.

Yep, that's a sign of a very insecure guy.  A lot of guys are like that, but most manage to hide it well. 

11. I asked him if he was tired (he works long long hours), but he said he was fine.

Was probably tired, but wanted to spend the maximum amount of time with someone he enjoys being with. 

12. I eventually said we should leave - he was shocked to see that it was 12.45am, and said how time flies.

13. He gave me a lift home (on his motorbike) and kissed me on both cheeks (he's Italian)

Probably catholic then as well, by the sound of his family values you mention above. 

14. I texted him to say that I was smiling and hoped he was too.

15. He replied saying that he'd just arrived home and was still smiling.

16. I saw him the next day ... and he beamed at me.

Really enjoyed his day and still couldn't hide the fact that it lights up his day seeing you. 

17. He emailed me in the afternoon to say it was one of the best mojito's he'd ever had

Ok, I'll presume he meant the food or the meetting and not something naughty.

18. He texted me on Friday just to say that he suspected I had the day off work (true)

Keeping up the contact, which is very positive. 

19. I texted him later that evening to say I hoped he wasn't still working

20. He replied that he was having a pizza, but he wouldn't be having a late night, and that his back seat would remain free.

Hint, hint, hint. 

21. On Monday afternoon, he emailed to ask how my weekend was.

22. We exchanged some more friendly /lightly flirtatious emails

23. We went for dinner Thursday evening to a magical restaurant.

24. Had a wonderful evening, conversation flowed, laughter filled the air, and I was basically on cloud 9 without any assistance from the wine :-)

25. He gives me a lift home on his motorbike.

26. Arrive at my door, he asks if I have 5mins as there are a couple of things he needs to tell me...

And yes, you've guessed it, he confesses that he's not 'completely' free.I don't want to seem totally gullible, but I do think that he is a 'good' man rather than a typical Italian player. My colleagues who have known him longer than I seem to think he is a decent man.. although obviously they're not aware of the situation! I appreciate I could be totally wrong but... He basically said..

1. that he didn't want to go into his relationship issues at that particular moment (it was 1.00am at this point), but was on way to breaking up with her, but that he didn't want me to feel responsible ie. that it would be due to me that he broke up with her.

2. That he hadn't slept all the previous week for thinking about me, and how it would be to be with me.

3. That even though we'd only done simple things ie. drinks and dinner dates, he'd had the best time he'd had for years.

4.that before the first date, he hadn't been sure if it was just 'friends', after that, he realised it was more, and that he was even more attracted to me, and wanted to at least have one more evening with me before telling me.

Standard thing for a guy to do, see you as a friend and then make another date, to make sure it wasn't a one off night.  The fact that he had a good time with you on both occasions and hasn't stopped thinking about you, made his decision, that he likes you and needed to tell you that, but also needed to be straight with you about his relationship status.  It's very difficult for a man to say this, so you've got to admire his honesty.

5. Said that although we hadn't known eachother for long, didn't want to lose the friendship.. although being honest, he wasn't sure he'd be able to be friends with me as he'd never been in a situation where he had to try to be just friends with someone he really really liked.

6. That he had spoken to his brother about me and his brother had said that he knew it would happen because he (his brother) knew that he didn't love his girlfriend, and was just surprised it hadn't happened sooner.. to which 'my' chap said, because she wasn't working in the same office then.

7. That he didn't want to force me to make any decisions then and there, asked me to think about it and let him know.

Phew, ok, hope that's enough info!

So, the fact is, I have a 101 questions running through my mind, and I'd appreciate your thoughts on the situation.

Yes, he could be an Italian player, but by the sound of things he's made an attempt to be genuine.  This would have to be a damn good players plan, if this is the scenario he's worked out in his head.  So I think for now, you should be cautious but give him the benefit of the doubt.  If he really is interested in you, the way he says he is, then I think you could go on, to have a really brilliant relationship.  The question is, how long is he going to take to ditch his current partner.  You've had a brilliant time together and I don't see why you should stop yourself having a brilliant time with him, just because he has announced this.

You are going to have to be patient and wait for him to ditch his girlfriend and for that, you are probably going to have to pretend to be friends for a bit and continue to go out and have a good time.  If you continue to have a good time with him, that will make him more keen to finish his girlfriend sooner.  So I think you should continue as you are now and tell him you are happy to see him as friends and keep meeting up.  Then it's up to him to take things further, when he has finished his current partner.  You should of course be cautious about him because he could be adopting a very good player plan, but really I think considering his genuine good times and smiley face with you, I think it's something much more than that.  I think he really genuinely like you.

Reply by Tumultuous Turmoil 21.05.08

If you’ve got some more spare time, here’s the latest installment of my tumultuous love life!

On Friday, after reading your reply to my first message, I restrained myself from emailing him, and went home early to digest what you’d said. On Monday morning I arrive at work to 2 emails that he’d sent on Friday late afternoon. The first saying it was a sad day without one of our smiles, the second saying that  he couldn't put aside all those magical feelings while I was holding him tight on the bike.

I replied saying that I didn't really know what to think, say or do.

He replied that he was confused too, but optimistic,  that we only have to look each other in the eyes and understand what we really want. and that he thinks it's worth trying. 

As per your advice, I agreed to see him on the Friday. During the week, lots of lightly flirtatious, complimentary emails were exchanged.

We went to a classical music concert, and not exactly as per your advice, we became quite tactile..  In fact, our hands caressed throughout the concert.. which I admit was somewhat distracting!

Afterwards, we went to a bar for drinks.

He told me he'd spoken to another friend about me and that the friend(female) said that if he didn't finish with his girlfriend in a week, she would phone him every day until he did!

I asked him about his situation, he said

1.    he'd got together with her shortly after splitting up with a very very long term girlfriend (not unusual, he's Italian)

2.    he's never been sure if he loved her or not

So he doesn't love her unless he's lying to you for the sake of persuading you. 

3.    she'd broached the subject of marriage in the past, but he'd put a dampner on it

Because he's not ready. 

4.    they've been together about 3 years, but she only stays over a couple of nights a week

3 years and he still doesn't love her and hasn't married her, gosh he's certainly waiting for something better to come along.  The problem is when guys get past a certain point in a relationship it's much more difficult to get out of it, both mentally and physically.  He will think he's not really into her in one moment but he will have his attachment to her another moment.  He won't want to be alone.  So it takes one of two things to get him to finish her and that's for her to finish him or for him to have an affair with someone else and then her to finish him.  There is an outside chance that he would finish her, but for some reason guys just prefer the woman to finish things.  If he can he will continue seeing you whilst also seeing her, because really he has a mental block and would immensely miss her if he stopped seeing her suddenly, it would be like a bereavement.  All that despite the fact he doesn't love her and doesn't see her as long term.

5.    he went on to reel off the options he thought I'd have already considered - and was spot on. ie.

      I won't have anything to do with him until he's free

      I see him but give him a deadline for when to have broken up with her

      I don't have anything to do with him ever again regardless!

Typical Italian, he knows how a woman works quite clearly.

He also said that he really didn't want me to feel responsible for him breaking up with her,

This is more like manipulative behaviour, why should you feel responsible for breaking him up with her.  He's trying to put that idea into your mind, to make things more exciting. 

but that having met me..... and told me again that I didn't have to decide then and there what to do.

He's again putting ideas into your mind, so that you literally do think that.  This is more player territory

He also suggested that if I were to say I wouldn't have anything to do with him until he was free, it may well get him to take action sooner rather than later... is this because he’s emotionally weak and unlikely to get the guts to do the deed?

It's because he prefers the women to make the decisions for him.  If he'd only been going out with his lady for less than 6 months, then he probably would have had the guts to ditch her.  As it stands it will feel like a bereavement if he ditches her after 3 years, plus he doesn't know how to negotiate the break up without causing himself severe agro and making him feel guilty. 

As we were talking, and joking about something else or other, he put his head in his hands and said 'I can't believe I've fallen in love with my teacher'! I made some kind of joke about students, and ignored the four letter word! Was this a slip of the tongue or is he really thinking that, even if it is at this point only infatuation?

He's only been going out with you a few weeks, he's not in love with you.  Yes, he maybe confused about what the word love is, but really you don't fall in love with someone within a few months of going out with them.  Love is something special, it shouldn't be made into a cheap word, love means that you like someone so much you can see yourself being together forever.  That means you have to go through months of working out whether you are right together, whether you can truly spend the rest of your life together.  You can't just turn up on the scene and within a few weeks anounce you have fallen in love with someone, it's just false.  It's just trying to pull a woman's strings, most likely her panty strings.  He's starting to display the Italian player tactics now.

We stayed in the bar until 3am. I told him that I wouldn't be the 'other woman' and when he took me home, I told him that I wouldn't 'kiss' him. I texted him before going to bed, saying that I really wanted to kiss him, but only when he was mine to kiss, and thanked him for another wonderful evening. He texted back that he longed for it too, that when the kiss happened at that time, it would be all the more special and thanked me for showing him another piece of heaven.

He knows how to play with words in that romantic Italian way and I think overall he does sound genuine, despite adopting some of those player tactics.  Even more so, because he hasn't persuaded you into bed yet and because he can even hold himself back from kissing you.  Though ultimately he knows the more you hold back from kissing him, the more one day you are going to jump him and get seriously passionate.

We exchanged a few texts over the weekend and then on Monday morning he emailed me saying "I had a fantastic time with you Friday night. Both the parts (the concert and the talking at the bar) were so emotionally intensive that they still seem present to me. What impresses me more is that we are so spontaneous in every situation (in the sweetest as well as in the hardest). I mean that... being frank is the rule, but it has never been so easy and natural :-)"

It does sound like the start of a good relationship, because you are both discussing your concerns and being honest with each other.  And that is not creating great arguments causing you to cool off on each other, you are both accepting it as honesty.

He phoned me after I sent him an email because he hadn’t understood something I wrote. Immediately after the 4min call, he emailed saying

“I can’t get emotional just from a mere call. I’m 33!!”

Knowing he was due to go to Rome the following day, I emailed to wish him a good trip and jokingly said for him to try not to miss me too much. He replied jokingly in his email not to worry about him as he won’t miss me so much.. and then added a P.S to his mail saying that it WAS NOT true, and that he’d really love to visit Rome or any other place we’ve never been together, with me.

Again that's very nice, he's a professional at wording things.

I texted him last night saying that he should be warned about me… that I have a tendency to sing and dance around my bedroom to Barry White when I’m happy. He replied that he would be proud and that he will do his best to get me dancing around my bed ;-)

Hmmm, yes, good idea make her think about sex, some nice flirting there.

This morning he texted to say that he was on the plane, that his mobile should be switched off, but that he couldn’t resist .. good morning!

Again being romantic and spontaneous, trying to get more brownie points.

This all feels so wonderful, he’s so romantic and seems so sincere, but I need some grounded advice. I would like to see what the future holds for us, but I don’t want to get a broken heart waiting, if it’s more likely that he won’t leave his girlfriend, or that when he does try to break up, he agrees to give it one more chance..

I don’t want to give an ultimatum in case the date goes by but I don’t want to give in at that point..

I don’t know how to play it for the best.. but I want to play it for keeps.. or am I kidding myself that this guy will do right?

Again, it sounds as though it's going well.  You've had another good night out together, so I don't see any reason why you should stop having some good nights out together.  Yes, you should remain cautious because he's still with his girlfriend, but ultimately you are doing the right thing, no kissing until he finishes his girlfriend.  The longer you leave it the more likely you will find out whether he is genuine or not, because he will start to crack and his story will start to unravel on him if he's playing with you.  So again continue to convince him, that he would be better off with you by having a good time out together, but you've got to be cautious because ultimately he's still with his girlfriend and it's not the time yet to give him a successful ultimatum.

Reply by Tumultous Turmoil  23.05.08

Following my last email, I had a think and discussed with a girlfriend what to do next. I kind of decided that

1. the next time he suggested seeing me I would be unavailable. Not to play hard to get exactly, more to make him realise even if only subconsciously that I wasn't at his beck and call whenever he wanted and that I have my own life to live aside from him.

Fair enough. 

2. That  I would suggest another day and that when we did meet, to have another wonderful evening and at the end of the night, ask him where his head was at. Then, if he said he was undecided, I was going to say that I wouldn't see him again until he'd decided.

You are giving him an ultimatum far too early on in the relationship.  You are basically saying to him, we've met up for a few dates, now ditch your partner of 3 years.  Is he going to go for the partner of 3 years or someone he's been on a few dates with?   You need more time to get him hooked.

Or, if he said he was going to split with her, ask him what he was waiting for.

I think it's a good idea for you to ask him the question in follow up to what he is saying.  But I don't think it's a good idea to just ask him a question out of the blue.

Whichever response he gave, I was going to say that I was loving spending time with him but that I couldn't see him again until he was sorted as every time I see him I become more and more involved.

It's only fair that he ditches her, but to a guy that is a difficult decision.  He could lose his girlfriend of 3 years, go out with you for a few weeks and find that things are not working out with you, so then he's lost both of you and he's single and back on the shelf.  Whilst he should really and truely be fair to you, I think it will be a difficult decision for him to make.

How does that sound to you?

The question in follow up to a comment would be fine.  Not a ultimatum though!

Only thing is now, he emailed me this morning about another classical concert - an orchestra this time.. I would LOVE to got to. But, it's not until the beginning of June, and so, if I agree, aren't I kind of saying it's ok to just string me along????

Just say you don't know what you've got planned for June yet, so can you tell him closer to the time. 

Any advice from a screwed up romantic?
 

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