I’ve been reading your website with interest for a while and have found your responses to women’s dating dilemmas helpful.  I’d like to ask for your help with this problem and get a guy’s perspective. 

There’s this man who attends the same book group as me.  I’ve been attending for about 12 months and we meet regularly every few weeks with 6 others.  He’s definitely single.  But he’s quite a bit older than me (I’m 32 he’s 49 though I didn’t know that he was quite that old initially). 

With the age difference I think there is a greater degree of chance that he likes you, add to the fact that he is single and I think you've got a good chance of things happening. 

I’ve got the impression over the last 2 or 3 months that he likes me: agrees with things I say, blushed when I asked his advice directly, suggested I phone him if I needed any help chairing the next meeting

There's a hint for you.  It's also a hint that he feels he wants you to make the move, because he's so unsure whether you will like him.  A guy with such an age difference feels extremely apprehensive about making a move on a woman so much younger.  If it goes wrong, it makes him look like a dirty old man and he won't want to risk that.

(I did, but the conversation was strictly professional), sat next to me at the Christmas meal, looks he kept giving me.  Anyway, I decided maybe he’s shy and maybe I should make the first move; so after lots of procrastinating I sent him an email asking if he’d like to meet for coffee and giving him my phone number. 

That is an excellent idea. 

Within a couple of hours of my sending the email he rings me, but I didn’t answer (I was at work, and I was too nervous to speak to him),

Not answering once would make him nervous and apprehensive, but he'll give you the benefit of the doubt and call again.

so he rings again in the evening.  We don’t say very much,

That's because he wants to save the chat until coffee.  Chat too much now and you'll have nothing to say over coffee. 

he just says that he would love to go for coffee (and I thought his voice sounded different) and we arrange to meet in a 2 days time.  I was worried that he might misunderstand and think it’s to do with the group rather than because I like him. 

We stayed in the coffee shop for about an hour and a half; chatted about various things including our jobs, hobbies.  But bear in mind that he does already know a certain amount about me from our meetings and things said to the group.  Though I’m a bit disappointed he didn’t probe further. 

Oh, yes. 

[This bit censored because it could reveal your identity.] 

From the bit that you censored, I guess his joke about age reveals several things, it suggests that he feels too old for you and therefore won't make a move, it suggests that he's trying to get your opinion and the silence that followed made him slightly uncomfortable.  He probably regretted making the reference because he won't want to put into your mind that he is too old for you. 

If I want to take it further, is it up to me to make the next move? 

Unfortunately, yes, with this amount of age difference and a gentlemanly type of guy, he's not going to make the move, because it will make him feel like a dirty old man and he won't want to risk that.  It is likely that he fancies you and his thoughts will be more along the lines of really fancying you but believing you almost certainly won't be interested in someone as old as him. 

I was hoping he might have rung me.  Especially as I ended up paying for coffee, he didn’t even offer!  Was he just being rude, or did he not want to seem presumptuous? 

I think the presumptuous option is more appropriate.  When you are not dating a woman, you feel rather self conscious paying for drinks as if trying to indicate you want to be an item.  It always amuses me because if a guy asks a woman out she presumes it rude if he doesn't pay for everything, if a woman asks a guy out she still presumes it's rude for him not to pay.  Though I would have hoped he'd offerred to at least pay his half rather than all of it.  He probably even thought, coffee doesn't cost too much, if it was something more expensive I would risk paying for it and look as though I'm wanting to date her. 

You’d think that it might be a good excuse for him to get back in touch and say I owe you a coffee… 

He wouldn't think of that excuse. 

When we left we walked out together; I can’t remember exactly what was said as we parted but just that he’d see me at the next meeting. 

Do you think he’s just not interested, or only as friends? 

He's more than likely interested, it is possible that after meeting up he decided that maybe you weren't right for each other anyway.  But if you got the impression that you got on really well, then I certainly think there's a good chance he will like you.  His mention of his age, might have floored him a bit and dented his own self confidence, he probably regretted saying that and if he did that would be dwelling on his mind for the rest of the meeting.  Really though a meeting like this needs to be fun, relaxed and full of flirting.

I know he’s tried dating before (personal ads etc) and presumably nothing happened long-term.  Do you think he’s reached the stage where he’s put romance behind him? 

If he's tried dating and hasn't found anyone, I think he will be very apathetic about meeting women.  He will have been through some bad times whilst dating and lots of women would have messed him about, lots will have rejected him.  That would dent his self confidence but also make him think, I'm more happy being single that putting myself through this agony. 

I know he’s got plans to go travelling in the future and I wouldn’t want to stop him (might be nice to go with him).  It doesn’t really matter for me if I start something with him or not – I’m making plans to change my career and may have to move temporarily but this won’t be for another 3 or 4 months (he doesn’t know this).

I think you need to make the moves.  You need to see how friendly he is at the next meeting.  But don't try and avoid him or automatically think he's been funny.  Something about your coffee meeting might have made him feel insecure about whether you like him or whether he said or did something wrong, believe me, men never tell anyone about their insecurities but they are there in their mind, just like a woman has her insecurities.  After a few weeks or standing back and seeing his reaction to you, then it might be time to make another move, depending on his actions in those few weeks.  You should continue to be friendly with him and make it known to him that you welcome his company.

Reply by aliceinwonderland 28.04.08

I wrote to you a while ago about dating an older man.  We’ve met a few times for coffee, but arrangements have always been made by me and he’s never refused.  And yes, he has taken his turn and paid!  Even brought me a second cup.  I’m still confused as to whether he likes me and if he’s being shy.

Well, he's eager to meet you each time and must enjoy his time with you, if he offers a second cup.  So there's certainly something there, whether it be he fancies being close friends with you or fancies being more than that.  My suspicion by what you have said so far, is he is probably being very cautious and doesn't want to scare you off by making a move.

I decided to up the ante and go from coffee to an evening ‘date’ where we have something to eat together, but go somewhere informal for a pizza or similar.  It’s difficult to think of somewhere to go because he doesn’t seem to drink alcohol so a bar or pub is a waste of time.  But I dithered so long about phoning him, that I left it late on Friday afternoon and just got his work answerphone, and I just left a message saying that I was calling to speak to him and left my mobile number.  I suspect he’d gone home for the weekend (he runs his own business), but as I don’t have his mobile or home number I can’t ring him there.  What is about shy guys not giving out mobile numbers?!! 

First of all it's like saying to a woman, here I fancy you, have my mobile number.  But also what guys are scared about, is that women are going to endlessly text and phone him at random times when he is busy and maybe not in the mood for chatting.  Whereas if he has your number he can control when he phones you, so he knows he's ready to speak.  I think it's because shy guys are so shy, they don't know what to say when they are put on the spot and when they do say something it usually ends up sounding wrong. 

I know a few people have tried to get it from him, but he just made the excuse that he regularly changes his phone!  Should I try and wrangle a number from him? 

Men don't particularly like giving out their phone number until they are in a relationship.   But there's no reason why you shouldn't at least ask, he can always say, no.  You can tell him you tried to phone his works phone, but he'd gone home, so it would be useful if you could contact him on his mobile phone.  Don't give him the impression though, that you are going to phone him up at random times and talk incessantly.  Men prefer to talk in person, not into some bit of plastic or metal they have in their hands, to a man a mobile is for urgent and essential stuff, that can't wait until you next meet.

He rang me on Sunday, but I didn’t get his calls as my phone was left on silent, and I didn’t realise it until late that night, so I sent an email asking him out for a meal one evening; he rang again Monday am but I couldn’t answer, so he rang again after work, always from his work number. 

Again, this constantly not answering, although accidental, may make him feel you are giving him the run around. 

I piked out asking him for a meal and said how about coffee again this week.  He said he was busy with work this week, but could do the following week, so we made arrangements.  I happy to keep things going along, but I feel that he’s not taking the initiative is a sign that he’s not interested.  I’m not that experienced with dating, but I’ve usually found the men I’ve been out with much more forward and proactive at making moves. 

He's probably enjoying the fact that you are making the moves, but there comes a time when he really should start reciprocating. 

Not that that’s always a good thing as things can move too fast.  Similarly, it’s always been pretty clear we’re on a date, whereas with this guy, I’m not sure it is clear. 

He may think you see him as a friend, and therefore he doesn't want to scare you off by making a move on you.  But even as a friend you would more than likely ask someone out, rather than relying on the other person.  You said in your last message he's been dating plenty in the past.  Men can become pretty apathetic and cautious after dating, because he will be used to women messing him about after he has made the moves.  For example in my experience if you show signs early on of really liking a woman, she usually backs off and is not interested in you, even if you did have a great time on the date and she seems interested.

I don’t know if he got the email, he didn’t refer to it so I presume not.  Or maybe, he’s trying to let me down gently?  But then why is he prepared to spend time with me? 

He wouldn't be prepared to spend time with you, unless there was a need for it.  Time is precious to a bloke and he won't waste it on women that are not worth it, either from a friend point of view or potential partner point of view.   A guy will be pretty blunt and avoid you completely and won't lead you on, unless he feels as though he's going to get something out of it.

Am I just friend material?  He does look at me a lot, checks out what I’m wearing, or when we’re out having coffee looks at me quite intently but I get embarrassed by his gaze and drop eye contact (I know I’m not supposed to do that). 

It's not so much that you are not supposed to do that, it's more that some guys might see it as a negative signal.  The truth is, that is a natural reaction for a lady.  A lady should break off eye contact first and do it in a submissive way, and that's what you are naturally doing. 

Or am I not being obvious enough that I like him?  I’m rubbish at flirting.

I think you need more time together to work out what's going on.  It could be that he's being cautious and with time he'll begin to realise you are worth taking a risk for.

But how do I get him to take the initiative?  I would like him to call me up and invite me out somewhere, perhaps on a ‘proper’ date.  I’m not sure if you would call coffees or lunches we’ve had so far a date…  we don’t behave as if on a date, more as friends getting to know each other.  Which is good.  But I would like things to progress, perhaps even kiss him.  And he does make an effort when we meet at these times: wears clean, smartish clothes, is clean shaven and wears aftershave.  So that’s a good sign, right? 

Yes, because why wear aftershave if you are not interested in someone?  He'd have to be wearing it for you or the waitress in the coffee shop. 

If we meet with others in our book group, he doesn’t necessarily do all of those things (e.g. misses off the aftershave). 

You've spotted a very unique but subtle difference in his behaviour towards you.  He's not giving much away in other respects, but this is a give away, the aftershave is there for a reason.  To signal to you, that he wants to smell nice in your presence. 

Equally, he tends to stand quite close to me, but to one side or behind if we’re walking along or in a queue, which is weird (I don’t like talking to someone behind me).  I tend to dress fairly casually too when I meet with him, though he has seen me at other times in work clothes (skirts and suits) so it won’t come as a massive shock to him if I don’t wear jeans J . 

Work clothes tend to be a bigger turn on to a guy initially, it's only later on when guys prefer to see women in a nice dress or a nice top.

In a couple of weeks time, we have a meeting with our book group and we are going out for drinks afterwards to celebrate my birthday.  So I’m pretty sure he’s going to be there ;)  I thought this might be an excellent opportunity, don’t know what though…  But, he’s very shy with other people around, although I get a proper smile now.  If I’m walking on my own he’ll catch me up and talk.  But at the last meeting I was late (I’d had a job interview earlier, which I’d talked to him about) and he gave me a nice smile, afterwards, I hung back to talk to him, but he was waylaid by someone else, and when they caught up with us, we all chatted together briefly and then went off.  But why didn’t he talk to me specifically, ask how things went (it wasn’t a big secret) instead of disappearing off? 

Not the right time or the right place.  Men just don't think of those opportunities. 

At the meetings we tend to sit around a largish table and I have always sat opposite him (well, it means I can watch him and he’s in my line of sight…) though perhaps I should contrive to sit next to him. 

I think sat opposite him is a good way to start things because it means you can naturally sit and look at each other from a safe distance.  As time goes by though you need to start sitting near each other, in touching distance and invading each others space, to test your ability to be in close proximity to each other.

I wonder if he thinks I’m too young? 

Probably, That's what I always think of women that are more than 8 years younger.  I don't think there's any point in making a move, because I'm happy to have them as friends, because I find it too much of a dream to even consider that someone as young as that would even consider fancying me. 

He doesn’t know exactly how old I am (well, it’s not easy to work into the conversation), though he has been fishing for information, ‘so have you always done x or have you had other jobs too’.  It doesn’t help that I look young for my age and have a totally inability to add up, so when talking about some past event I knock too many years off (i.e. saying something was 10 years ago, instead of 14). 

I think we all do that, I can't even remember what I did last week, let alone whether something happened 10 years ago or 2 years ago.  Once people get to the age of 25, there memory deteriorates year by year.

So, I think he’s finding it tough to work me out!  I don’t particularly behave in a young manner or talk in a slangy way, or dress like a teenager.

I think he probably will need some convincing that you like him.  But as time goes on, more opportunities to get to know each other and do things that hint at being comfortable about touching and talking intimately are ultimately going to happen.  You just need to be patient and gradually work some hints into the situation.

Reply by aliceinwonderland 08.05.08

I met up with this older guy again for coffee after work.  It was a weird meeting; I wasn’t feeling particularly well, but I wanted to see him again.  We made small talk and caught up with what each other had been doing over the last couple of weeks.  But there were a couple of odd points where I thought he was trying to push me away (perhaps wanted to see if I would react) and another where he seemed to suggest that we were in a sort of relationship.  He has big plans to go travelling, it’s pretty serious he’s renovating his house to sell, he’s fed up with his work (he’s self employed) and wants to wind that down, getting rid of possessions in order to fund and free up time. 

[Censored some information to protect your identity] 

Okay, so he seems pretty serious about doing this and it’s his childhood dream.  So, I listen to this and I think well I don’t want to stand in your way and hold you back.  So why’s he telling me this.  Is he trying to provoke a reaction, like don’t go, or can I come with you?   

It's for several reasons.  He wants to see if you encourage him and seem keen to have that lifestyle yourself, after all he would love someone to spend that time with him.  But he might also be fishing for ideas about whether you fancy him, if you seem keen and say, I quite fancy doing that, he may think, ah, so she likes me and fancies joining me.. 

I’ve just told him that I think his plans sound great.  But I think to myself there’s no point trying to pursue anything as he’s trying to cut ties and leave the country in a few months.  So I think well there’s no future here. 

He will debating that as well, is there any point in getting with her, if I plan to leave the country.  But then if he thinks your worthwhile he will either stay or else try and get you to come with him.  The guy is obviously fed up with his current life and wants to do something about it, you only have one life and have to make sure you enjoy it, he wants to enjoy it whilst he can.  He'd probably prefer to spend that enjoyment with someone else, but really that depends on whether that someone else is interested. 

The we move onto other topics of conversation.  But he has to go after about an hour because he has to babysit his niece and nephew, so our long rambling 2 hour chats are cut short.  I ask how old they are.  Then he says the oldest boy he doesn’t see much of because he has a ‘lady friend’.  He explains that they are not ‘boyfriend’ and ‘girlfriend’ yet; and that things have changed with young people in that they don’t become boyfriend and girlfriend straight away, they start off as friends.  I didn’t say anything, just laughed and went Hmm.  (I was a bit slow on the uptake cos I wasn’t well). 

Yes, I think this is his thoughts.  He's probably been through loads of nightmare relationships, where things got too serious too soon, now he carefully vets any woman before stating he is in a relationship with them. 

But then I thought afterwards is he making reference to the 2 of us - the fact that we keep meeting up.  Am I reading too much into it? 

There's a chance that something like this will slip into the conversation and he just spoke spontaneously, but really even if he did speak spontaneously there is an element of his own thinking there.  It could be him thinking in various ways, like critisizing the fact that women only want to be friends at first or a hint that he wanted to take things slowly and check you out for a bit before declaring a relationship. 

It seems an odd thing to say.  Does he see us a friends rather than potential lovers?

No, having said that, if it was a hint, then it was a hint to say at the moment we are just friends, but friends has the potential to move towards being lovers.

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