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He's 56, I'm 27. Should I tell him I love him?


HabGirl

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I started working for this construction company back in the summer of 2006 and he is a foreman of this company. I talked to him every week for payroll related issues on the phone and always liked his phone manner - he is a U of T graduate, a deep thinker and a gentleman. I was 24 back then and he was 53. I first met him at the end of 2006 during our company party and I was attracted to him immediately. He is a handsome guy and he's in perfect shape for his age - He's a Marathon runner and this past week he just finished first in his age group at the Miami Marathon.

 

I always talked to him about troubles at work and he has been a very good listener. He just has such a calming effect. The second time I saw him was end of 2007 at the company party again and I was more convinced that the physical attraction is definitely there.

 

Since he is a runner, I went for a 5K charity run with him in April 2008, which marked the third meeting between us, although we've been talking regularly over the phone. I also took him out drinking on his birthday during the summer and then we had another charity run together in October. We always enjoyed each other's company but with every meeting the comfort level grows and we've developed a very strong and unique connection.

 

We started dining out together since October 2008. Every two weeks we'd meet at a fancy restaurant and spend a night talking and drinking till 2 am. He would always walk me to my door and hug me good night. Over the holiday season we had to attend a funeral together (our boss died) and that was that night we were both very mellow after drinking a few glasses of wine. He was holding me hand the entire time when we were walking to the parking lot. I felt very happy that night. We would finish every date with a long hug, then I will dream about kissing him when I sleep.

 

To sum things up, we got to be very close during the last 3 months and we spend at least 10 hrs a week talking on the phone. I do feel that I am madly in love with him and he adores me too. I don't know what to do now. I want to get closer - but he is 29 yrs my senior. He had mentioned once that he would definitely have a relationship with me if I'm 15 yrs older. He also mentioned that he'd marry me if his physical comes back with bad news (half jokingly) so I could have his estate (he never married, no children).

 

I am Chinese-Canadian and he is white. My parents have been urging me to find a viable marriage candidate, but they don't know about him. I know very well that they'd be against it if I ever develop a relationship with this guy. I don't know what to do. I am tortured by the feeling of missing him everyday. I would like to tell him how much I love him but I don't wanna risk losing him as a friend. What should I do now?

 

Sorry for the long story. My thoughts are not organized. Any advice would be appreciated!

 

Thanks!

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Welcome to eNotAlone.

 

I think him saying he would have a relationship with you if you were 15 years older could have been leaving you an opening to say that the age difference isn't an issue for you.

 

But if you want to proceed with this guy think through all the issues that will arise. Not just your parent's opposition but the fact that when you are forty he will be sixty-nine and retired. Will he want children? Will you be OK with being a widow early (assuming normal life-spans)?

 

Think through the negatives and if you know you want him anyway - then proceed. You will have to initiate something though because I doubt he will.

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You are playing with fire. You have a crush on a much older gentleman who is one of the bosses at work. You might end up being his sex partner as this continues but probably not his wife...not unless he is looking for a trophy wife. I am sure your family would be very upset if they learned about it. They would not want you to be with someone old enough to be your father. Think about this long-term, not the short-term emotions.

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If you really care for this man. I would just go for it. But are you sure that this isn't just a fatherly type of relationship? If not I don't see the problem, live YOUR life, and your parents would have to accept it or not. Just make sure you know the company policy on dating. =D

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Thank you DN!

 

You're from Ontario, too.

 

I'm just worried about making things awkward between us. I think he knows how I feel about him. I've been through a few short-lived romances during the pass year or so and he's always my best supporter and always helped me through my emotional roller-coaster rides. We talk about doing lots of things together and it seems to me that we're made for each other in many ways.

 

I wonder if me telling him my feelings might ruin what we have now.

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Well, don't blurt them out. Just show that you are attracted to him a little more and see what happens. Don't rush the fences.

 

I think that he is probably concerned too about the age gap and it appears he has acted like a gentleman so far in not pushing for more than friendship.

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You are playing with fire. You have a crush on a much older gentleman who is one of the bosses at work. You might end up being his sex partner as this continues but probably not his wife...not unless he is looking for a trophy wife. I am sure your family would be very upset if they learned about it. They would not want you to be with someone old enough to be your father. Think about this long-term, not the short-term emotions.

 

Oh, you misunderstood. He is not my boss. We work for the same company but he doesn't have any power over me.

 

He had never made a move on me. When we talk it's basically about our common hobbies like running, music and books. He's been more than a friend. He is always there when I need to talk and he wouldn't say anything inappropriate.

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He sounds like a great guy but in my honest opinion there's a huge age gap. I'm assuming you thought of every scenario, even if you two end up together what would happen 10, 15 or even 20 years from now. If you two can live with the differences and lifestyles that I'm assuming going to change for both of you (age wise) is it something you can live with?

 

I know age is nothing but a number but when you're 47, he'll be 76. If you're looking for a long term relationship it's something you should seriously consider. And I only say this because of someone I liked for a long time (years ago) was 15+ years older. Now that I think back, things would've changed drastically with time and not sure if our relationship would've worked out in the end.

 

As far as telling him your feelings? Honestly go for it. I'm sure he already knows

 

EDIT: I'm pretty much in agreement with DN.

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Thanks for the reply!

 

I've seen my parents fight through the years. They're both 53 now and they haven't had sex for 5 years. I've witnessed lots of marriages gone bad and I no longer dream of "happy ever after" marriage.

 

When I was growing up my dad was not around (he was traveling around world working). Maybe this is why I always like older men.

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If you understand and have weighed the ramifications and still feel strongly about him and being with him, then I say go for it.

 

However, if you have considered all the factors and you're still in some doubt, or the doubt and worry outweigh your love for him then clearly I would say park it and keep him as a friend only.

 

What do your friends think? Have you confided in any of them?

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If you understand and have weighed the ramifications and still feel strongly about him and being with him, then I say go for it.

 

However, if you have considered all the factors and you're still in some doubt, or the doubt and worry outweigh your love for him then clearly I would say park it and keep him as a friend only.

 

What do your friends think? Have you confided in any of them?

 

We have a friend in common from work. She has seen us together a few times and she's all for it. She encourages me to go out with him even marry him.

 

I haven't told my other friends yet. I don't think they'd understand and I don't really care how they feel about it.

 

The only thing is that he said a few times that he's not a viable candidate and he has no claim on me. I don't want to embarrass myself by confessing my love for him. But the way he treats me is evident that he has strong feelings for me.

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he's not a viable candidate and he has no claim on me

Again, this is your opportunity to tell him you don't think he is right about the first and you wouldn't mind if he did have a claim.

 

But, as I said, think through the ramifications of this.

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I agree with what DN was saying earlier, he may be waiting for you to initiate or hinting and leaving an opening for you to do so.

 

I'd stew on it, thank hard for a week, then make the move if that's what you decide. Sorry, I know it's not that simple, but no point in waiting that long right?

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The only thing is that he said a few times that he's not a viable candidate and he has no claim on me. I don't want to embarrass myself by confessing my love for him. But the way he treats me is evident that he has strong feelings for me.

 

This is probably him not wanting to embarrass himself by confessing his love for you because of the age difference and him not wanting to feel like he's taking advantage of you.

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I have mixed feelings...

 

On the positive, you have taken your time and it seems genuinly built up a connection with him. I have known large age gap relations that went perfectly well (20 female, 43 male), and ended due to things totally not related to age. It sounds like a relationship has plenty of chance to thrive.

 

On the negative, are you seriously a HABS fan in TO?! Good god. If he's a Leafs fan.. well.. maybe you shouldn't bother

 

(yes, im from/in TO)

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I have mixed feelings...

 

On the negative, are you seriously a HABS fan in TO?! Good god. If he's a Leafs fan.. well.. maybe you shouldn't bother

 

(yes, im from/in TO)

 

Hahahaha Lecturer that's funny. I'm from TO as well and this is a TOUGH town to be anything but a Leafs fan (and no, I'm not a fan of either). Anyways, sorry, this is off-topic.

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This is probably him not wanting to embarrass himself by confessing his love for you because of the age difference and him not wanting to feel like he's taking advantage of you.

 

 

I may be blind now. It might be my wishful thinking that he has strong feelings for me.

 

Do you guys think it can be pure friendship on his side? I think he has love interest in me judging from the facts:

1. He spends 40+ hrs on the phone with me every month.

2. He is always my best listener and life coach.

3. When we go out together he would stay up till 2 am. Sometimes he end up getting home at 4 am because he has to take me home first. He'd never leave me to go home alone.

4. We would make very suggestive remarks through text messaging. But in real life he's all serious and respectful.

 

He must have feelings for me, right?

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I may be blind now. It might be my wishful thinking that he has strong feelings for me.

 

Do you guys think it can be pure friendship on his side? I think he has love interest in me judging from the facts:

1. He spends 40+ hrs on the phone with me every month.

2. He is always my best listener and life coach.

3. When we go out together he would stay up till 2 am. Sometimes he end up getting home at 4 am because he has to take me home first. He'd never leave me to go home alone.

4. We would make very suggestive remarks through text messaging. But in real life he's all serious and respectful.

 

He must have feelings for me, right?

 

You know, he very likely does, but you'll never know until you initiate or ask him first. When you've thought it through and if that's what you want, then sit him down and ask him straight up. I know that's hard, but that's the only way you'll know for sure. But yeah, seems he's interested but hesitant to pull the trigger (probably for many reasons; maybe he's shy, maybe he's concerned about the age gap too, maybe he doesn't wanna cause drama with you and your family, etc. etc.).

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I have mixed feelings...

 

On the positive, you have taken your time and it seems genuinly built up a connection with him. I have known large age gap relations that went perfectly well (20 female, 43 male), and ended due to things totally not related to age. It sounds like a relationship has plenty of chance to thrive.

 

On the negative, are you seriously a HABS fan in TO?! Good god. If he's a Leafs fan.. well.. maybe you shouldn't bother

 

(yes, im from/in TO)

 

Hahahaha Lecturer that's funny. I'm from TO as well and this is a TOUGH town to be anything but a Leafs fan (and no, I'm not a fan of either). Anyways, sorry, this is off-topic.

 

LOL. Yes I am a Habs fan and he is a Leaf fan.

 

Our first dinner together was the result of Habs beating the Leafs. We started betting since the beginning of this season and he has lost more dinners to me

 

I'm going out with him this Friday again to celebrate his return from the Marathon. It's also a free dinner won from Jan 8th when Habs beat Leafs 6:2.

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LOL. Yes I am a Habs fan and he is a Leaf fan.

 

Our first dinner together was the result of Habs beating the Leafs. We started betting since the beginning of this season and he has lost more dinners to me

 

I'm going out with him this Friday again to celebrate his return from the Marathon. It's also a free dinner won from Jan 8th when Habs beat Leafs 6:2.

 

Is that fair? Hahaha...he must know he'd lose the majority of those bets, given that the Leafs have been horrible for years and the Habs have been great the past couple!

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Is that fair? Hahaha...he must know he'd lose the majority of those bets, given that the Leafs have been horrible for years and the Habs have been great the past couple!

 

I know it ain't fair. I initiated the bets and he never turned them down. I just use them as excuses for seeing him and we just can't have enough of the dinners.

 

I took him to a Karaoke bar and I sang "Desperado". He seemed to be moved by the msg "you better let somebody love you before it's too late", but he kept his cool.

 

Oh I cried a lot last time I saw him because he was going to Miami to run the marathon. He wiped my tears for me and said that I am such a "sweet lady". I kissed him on the cheek when I hugged him good night. I have this irresistible desire to kiss him on the lips. I am crazy for him!

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Oh I cried a lot last time I saw him because he was going to Miami to run the marathon. He wiped my tears for me and said that I am such a "sweet lady". I kissed him on the cheek when I hugged him good night. I have this irresistible desire to kiss him on the lips. I am crazy for him!

 

Well maybe you should take the chance then, you've waited so long...think it over but...sounds like it's gonna happen anyways.

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Hi all...

 

I am new to the forum.

 

I would say to the OP, go for it!!! I have always dated older men even much older men as in the situation you are describing. It sounds to me like he is genuine and really cares for you. What really matters is how you feel about each other but also it is important to remember that there is a lot of resistance to these types of age gap relationships from family and friends. Be prepared for some harsh words and maybe even to lose some friends who disapprove. People can be very closed minded. When I was dating a much older guy ( I was 24, he was 48) I really had to cut some people off because they were so hurtful.

 

Also, I would not be concerned about the whole he will be X years old and you will on be Y years old and he will be old and retired, etc. I know many couples with considerable age differences including one where the wife is in her 50s and the husband in his late 70s and he is just as healthy and active as the 50 year old men in their social circle. Medicine has made great advances in recent years (i.e., viagra, etc) and there's lots of promising new drugs in the making. Also, since he is retired, he has a lot more time to devote to her, their home, their shared interests/ hobbies and travel where many of the 50 year old guys are still working 60 hour weeks and are consumed by their careers.

 

Best of luck to you!

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No worries! I guess I am curious how it will turn out as I know someone else in an age-gap relationship (but definitely not as wide...29 years is a lot) and same cultural difference. Sorry to be nosy. My PM isn't enabled, but if you want to hear more offline you can mail me (roto_copy@link removed). Good luck!

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