Should I tell him I want to date him?

[Ellin]

Hi everyone.

I am not dating but I would like to. I'm a single parent of several kids aged 7 to adulthood, I have had bad relationships but never given up on love. I've been single now for over a year. Recently I met a nice guy via mutual friends. I really like him and feel very good in his company. We've been seeing each other once a week / once a forthnight for coffee etc since early June. I was the one who suggested meeting up but he has been acting quite keen since. He has a lovely personality, is warm, caring, intelligent, funny, polite. What has gone on between us is strictly within the realm of friendship, all very proper.

There are a few issues, though. He is 14 years older than me and it is a bit of a problem for me. I'm in my late 40s (young looking and feeling, energetic, attractive sporty lady), he's in his early 60s. He had a difficult upbringing due to his mother's mental health problems and this prevented him from having successful romantic relationships. He only had one relatively short relationship and that was more than 10 years ago. He is kind of shy and reserved. Also he has some health issues which can potentially cause problems with intimacy (I googled the illness to find out more). So all in all it doesn't seem likely that this can turn into a romantic relationship.

I am certain that he will not make any move to turn it into a romantic relationship - I would have to take that step. I just don't know how to approach it. It is possible that he would not even want that due to all the above reasons. I'm looking for suggestions here. Should I just say it plainly that I am developing feelings for him and ask if he's interested in a relationship? Or should I try subtle hints, give compliments? I already wrote to him things like "It was nice to see you, I enjoyed it" etc, but he did not respond in kind. He would email more factual things about what he had been up to and about arrangements to meet again. Maybe try being vulnerable, make him know that I need him, that I value him and see if he responds to that at all?

I don't have any big intentions or expectations, as in having a whole future planned with him, I'd just like to see where it can go. I am enjoying his company especially because he is the first man that I am interacting with fairly closely, who is not abusive or difficult in some way. I would like to explore that more. I am feeling attracted to him and would like to get close, get physically affectionate and if possible, passionate. I'm wondering if this ship has sailed with him, though, based on his situation and history  - his age, health, being probably set in his ways and most likely deep seated fears regarding romantic relationships.

Any thoughts, advice?

[Weezy1973]

12 minutes ago, Ellin said:

Any thoughts, advice?

This jumped out at me:

 

12 minutes ago, Ellin said:

Maybe try being vulnerable, make him know that I need him, that I value him and see if he responds to that at all?

Why do you need him? That seems like an unhealthy place for your mind to be. 
 

My suggestion would actually be kind of the opposite. It seems you’ve tried subtly to escalate this, but he hasn’t responded. This looks to me like a potential friendship and not much more. You already see a lot of reasons why he might not make a great partner, and he hasn’t displayed any interest in anything romantic. Why push for something that isn’t there? 
 

I suspect you’re lonely and looking for someone to fix that, and this guy happens to be around. Not a great reason to start a relationship.

Edited October 4, 2022 by Weezy1973
Spelling

[glows]

What’s holding you back? I doubt he’ll be offended or taken aback. He wouldn’t be meeting with you if he didn’t already like you or enjoy your company. 

I wouldn’t say anything about a relationship as it seems like jumping too far ahead. 

Change the coffees to something else or suggest doing other things - go on walks, visit galleries and museums, see some festivals together and do more things around town. The coffee talks are fine but sounding more and more like a therapy session and getting too deep. Give yourselves a chance to loosen up and do other things.

[Ellin]

45 minutes ago, Weezy1973 said:

This jumped out at me:

 

Why do you need him? That seems like an unhealthy place for your mind to be. 
 

My suggestion would actually be kind of the opposite. It seems you’ve tried subtly to escalate this, but he hasn’t responded. This looks to me like a potential friendship and not much more. You already see a lot of reasons why he might not make a great partner, and he hasn’t displayed any interest in anything romantic. Why push for something that isn’t there? 
 

I suspect you’re lonely and looking for someone to fix that, and this guy happens to be around. Not a great reason to start a relationship.

Maybe I phrased it wrong. I don't need him desperately but his presence in my life is a positive thing, it cheers me up. I am lonely in a way and could do with another close friend, even though I have a lot of aquantainces, a few friends, my kids and hobbies and my life is full. It's not that he just happened to be around, you're totally wrong about that. I could be with a lot of men, but I rarely feel attracted to anyone,. I do feel attracted to this man and that's why I want to pursue this. That is also why it would be difficult for me to just vstay friends with him since I want more.

Thanks for replying.

Edited October 4, 2022 by Ellin

[Ellin]

2 minutes ago, Ellin said:

 

 

Edited October 4, 2022 by Ellin

[Wiseman2]

1 hour ago, Ellin said:

he's in his early 60s. he has some health issues which can potentially cause problems with intimacy 

I am certain that he will not make any move to turn it into a romantic relationship - I would have to take that step.

Make sure a romantic relationship is what you want with him rather than friendship/companionship. He doesn't see like a good candidate for romance. If he were interested in (or capable of) that, it would have happened already.

Edited October 4, 2022 by Wiseman2

[Ellin]

2 hours ago, glows said:

What’s holding you back? I doubt he’ll be offended or taken aback. He wouldn’t be meeting with you if he didn’t already like you or enjoy your company. 

I wouldn’t say anything about a relationship as it seems like jumping too far ahead. 

Change the coffees to something else or suggest doing other things - go on walks, visit galleries and museums, see some festivals together and do more things around town. The coffee talks are fine but sounding more and more like a therapy session and getting too deep. Give yourselves a chance to loosen up and do other things.

Thank you, Glow. We have been on a couple of walks, it was nice. It wasn't always very deep either, but he seems to have no issues with opening up. In the group of friends where I met him first, he was already telling everyone about his childhood and other difficult experiences, which I found a bit surprising. We could do other fun stuff, but even then I don't believe he will do anything relationshippy and it would have to be me to broach the subject eventually. But maybe you're right, having a bit of fun for a while would be a good idea.

[Ellin]

27 minutes ago, Wiseman2 said:

Make sure a romantic relationship is what you want with him rather than friendship/companionship. He doesn't see like a good candidate for romance. If he were interested in (or capable of) that, it would have happened already.

You have a point. But what do you mean by "Make sure a romantic relationship is what you want with him"? Did you mean he wants? I am sure I want that, even though I agree that he doesn't seem to be a good candidate for it. I can still try and find out, I'm just thinking of the best way to go about it.

 

Thank you.

[Ellin]

Ok, posting here is helping me clear my mind.

So... If it cannot go anywhere other than friendship, I do not want to continue in the same way. I would have to see him less often and focus my scarce free time on something that is higher on my importance list. I don't meet any other of my friends that often. This kind of frequency would have time in my life for dating.

Another reason I wouldn't want to continue in the same way is that I am attracted to him and I want more. If I'm supposed to just sit there with him and talk about random subjects, I would feel the discomfort of not being able to touch him when I want to. I miss physical intimacy and affection more than anything when it comes to what romantic relationships can add to our lives. I do want this in my life. I want sex but not just for the sake of it - I want it with a "special" person, which is not easy to find. I don't meet every day someone I feel like being intimate with.

I know it's ironic that I'm trying to get this out of a guy who seems to be the last man on the planet suitable for the job, but who knows? Haha. Maybe he would want to make up for all that time he lost.

I'd like to know.

[glows]

7 minutes ago, Ellin said:

Thank you, Glow. We have been on a couple of walks, it was nice. It wasn't always very deep either, but he seems to have no issues with opening up. In the group of friends where I met him first, he was already telling everyone about his childhood and other difficult experiences, which I found a bit surprising. We could do other fun stuff, but even then I don't believe he will do anything relationshippy and it would have to be me to broach the subject eventually. But maybe you're right, having a bit of fun for a while would be a good idea.

The emphasis is on fun, not locking this down. 

Some people self sabotage with TMI. I can’t imagine the oversharing and emphasis on his difficult past to be attractive in any way. He seems like a friend. This may fizzle out just as quickly after you realize the breadth/scope of his experiences or desire to want more is limited. You’re just getting to know one another but forcing this or want this badly to be something more physical. 

[Ellin]

4 minutes ago, glows said:

The emphasis is on fun, not locking this down. 

Some people self sabotage with TMI. I can’t imagine the oversharing and emphasis on his difficult past to be attractive in any way. He seems like a friend. This may fizzle out just as quickly after you realize the breadth/scope of his experiences or desire to want more is limited. You’re just getting to know one another but forcing this or want this badly to be something more physical. 

My goodness. What am I forcing?? I'm just wondering what is the best way to find out if it can go somewhere else than friendship. And how "badly" do I want this to be physical do you think? Because I think I want it in a pretty standard measure.

We've been meeting regularly for four months. People don't need to get to know each other for years before they start a romantic relationship. Often it's a week or so. You can get to know each other also when you're holding hands or cuddling, or whatever.

The reason I'm musing here about asking him this question is because I think he'd never do it, even if he wanted it.

[glows]

4 minutes ago, Ellin said:

The reason I'm musing here about asking him this question is because I think he'd never do it, even if he wanted it.

No, it doesn’t appear he would. My response was not meant to offend you. He’s too preoccupied with himself to be in a relationship and you’re emotionally attached to someone who doesn’t seem to share the same way you feel. If being friends is frustrating you and you don’t feel comfortable making the first move then it’s best to move on.

[poppyfields]

OP, imo you're overthinking this. 

Next time you're together, throw him a bone - a subtle look, a touch, a soft smile. 

Men always knew when I was romantically and sexually attracted and interested, I never had to say a damn thing. 

My energy, my vibe said it all for me.

If he doesn't respond, then trust me he doesn't want to respond.

At that point you have a choice, remain friends or move on.

Edited October 4, 2022 by poppyfields

[Ellin]

27 minutes ago, poppyfields said:

OP, imo you're overthinking this. 

Next time you're together, throw him a bone - a subtle look, a touch, a soft smile. 

Men always knew when I was romantically and sexually attracted and interested, I never had to say a damn thing. 

My energy, my vibe said it all for me.

If he doesn't respond, then trust me he doesn't want to respond.

At that point you have a choice, remain friends or move on.

Thank you, Poppy. I agree with you that any typical man would know by now, but he is not typical. He is a rare guy who has managed to get through this age with barely any experience with women. It's quite a good possibility that he's oblivious to this type of signals. I wonder often what he's actually thinking we're doing. I have been through something like that before when a guy was really interested but wouldn't have done anything if I hadn't made the first step and it had to be a clearer communication than a warm smile. The age difference between him and me was exactly the same.

Your suggestions are good, I will try and incorporate them.

If I find out (for sure) that he isn't interested, I will remain friends but considerably reduce the frequency of seeing him.

Edited October 4, 2022 by Ellin

[poppyfields]

14 minutes ago, Ellin said:

He is a rare guy who has managed to get through this age with barely any experience with women. 

He's in his 60s, correct?  

I wouldn't hold out much hope for him @Ellin.

I'm not a shrink but there's a reason he doesn't have much experience with women at his age, and it's not because he doesn't know how to read signals, it goes deeper than that. 

It leans more towards his anxieties and fears surrounding intimate relationships and at 60+, he's not going to change now.  

Or take steps to resolve. 

It appears he's quite comfortable in his single status, and the best thing for you to do imho is wish him well and walk away. 

Seek out men who are available for what you want. 

Choose wisely from the get-go and avoid pain and disappointment later.

He's not a wise choice imo, I'm sorry. 

 

Edited October 4, 2022 by poppyfields

[Ellin]

2 minutes ago, poppyfields said:

He's in his 60s, correct?  

I wouldn't hold out much hope for him @Ellin.

I'm not a shrink but there's a reason he doesn't have much experience with women at his age, and it's not because he doesn't know how to read signals, it goes deeper than that. 

It leans more toward his anxieties and fears surrounding intimate relationships and at 60+, he's not going to change now.  

Or take steps to resolve. 

It appears he's quite comfortable in his single status, and the best thing for you to do imho is wish him well and walk away. 

Seek out men who are available for what you want. 

Choose wisely from the get-go and avoid pain and disappointment later.

He's not a wise choice imo, I'm sorry. 

 

Right, thanks. But I did not actually ask whether I should drop him or not, I asked how to approach the subject as I would like to know his stance.

[glows]

4 minutes ago, Ellin said:

Right, thanks. But I did not actually ask whether I should drop him or not, I asked how to approach the subject as I would like to know his stance.

We see this on the forum all the time. A member wants to know or ascertain someone’s feelings before making a move or approaching the subject as a kind of insurance or guarantee of success. The truth is he’s showing you in his responses his interest in romance is lukewarm at best. You’re trying to look  for clues. Why don’t you just ask him what he thinks of dating and being in a relationship with you if this is the specific answer you need right now?  

[Ellin]

4 minutes ago, glows said:

We see this on the forum all the time. A member wants to know or ascertain someone’s feelings before making a move or approaching the subject as a kind of insurance or guarantee of success. The truth is he’s showing you in his responses his interest in romance is lukewarm at best. You’re trying to look  for clues. Why don’t you just ask him what he thinks of dating and being in a relationship with you if this is the specific answer you need right now?  

I am not looking to ascertain feelings before making a move. I am looking - as I have stated clearly in my first post and subsequent - for ideas what is the best way to find out from him in basically verbal communication whether he is interested in something romantic. If he isn't, I'm not going to put as much time and effort into him as I have been doing so far, that is all.

Thank you for answering my question.

Edited October 4, 2022 by Ellin

[poppyfields]

12 minutes ago, Ellin said:

Right, thanks. But I did not actually ask whether I should drop him or not, I asked how to approach the subject as I would like to know his stance.

His stance on what?  I don't mean to sound rude but isn't it obvious? 

60+, little to no experience with women, not making any romantic moves in four months.

Using your own intuition and common sense, what does that tell you? 

Do you really need to hear the words? 

I dunno, it tells me he's not available or interested and I know you didn't ask, but if you're smart (and available yourself), I'd wish him well and look for a man more available and desirous of developing a relationship with you other than friendship. 

That said, of course you do what's right for you, I'm simply providing my opinion about it. 

Good luck.

Edited October 4, 2022 by poppyfields

[Weezy1973]

You can always just ask him. Would he rather things between move to something romantic or did he see you as just friends? Straight and to the point. You get an answer and can then act accordingly. 
 

But something for you to ponder - why are you interested in a man that is unavailable? And by your own description not really a good candidate for a relationship regardless? What is it in you that seeks that?

[Hopeful30]

Hi @Ellin,

The approach depends on your personality and what you feel comfortable with. Do you prefer a direct approach? Or test the waters first?

You can open up to him (as a friend) about your desires to be in a relationship -- to experience physical affection and intimacy with a man. Ask him what he thinks. Here, you open him an opportunity to reveal if he feels the same, otherwise the opportunity is not understood. The answer will be clear.

This next approach involves deceit. Insinuate or suggest that you've been sexual intimate with a man recently, and observe his reaction. Lastly, catch him on a night when you look sexy. Allow him to see you in this light. Consider his response to you in this language. 

[Hopeful30]

36 minutes ago, Weezy1973 said:

You can always just ask him. Would he rather things between move to something romantic or did he see you as just friends? Straight and to the point. You get an answer and can then act accordingly. 
 

But something for you to ponder - why are you interested in a man that is unavailable? And by your own description not really a good candidate for a relationship regardless? What is it in you that seeks that?

Girl's got NEEDS, you know what I mean? 😆 we need loving too 😭

[poppyfields]

11 minutes ago, Hopeful30 said:

Girl's got NEEDS, you know what I mean? 😆 we need loving too 😭

Exactly.  That's why it's a total waste of time and effort pursuing these things with a man so clearly unavailable, such as this man. 

Aim higher.  Choose wisely. 

 

[Hopeful30]

9 minutes ago, poppyfields said:

Exactly.  That's why it's a total waste of time and effort pursuing these things with a man so clearly unavailable, such as this man. 

I meant sex lol!

Also, how do we know he's unavailable? 

Edited October 4, 2022 by Hopeful30

[poppyfields]

23 minutes ago, Hopeful30 said:

Also, how do we know he's unavailable? 

By his actions, or rather non-actions (over a four month period), and his history. 

His history:   60+, little to no experience with women or relationships.

To me, that combined with his lack of any romantic interest over four months, spells unavailable.

If it spells something different to you, then so be and continue pursuing. 

To @EllinI feel like I was rude earlier so to answer your question, you could ask him casually if he'd like to go on a "date."

Gauge his response. 

Good luck!

 

Edited October 4, 2022 by poppyfields