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Feelings for an older close friend


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My close friends and I have become good friends with this guy over the past year. I am 34 and he's 44. He has been single all this life (never married or ever had a girlfriend) because he's a workaholic. He's really shy and conservative though he's opening up now.

 

He started to be a little more outgoing recently and started going on dates with encouragement from our mutual friends. A girl whom he went on a date with is very interested in him and is around same age as me and based on his description, similar character to me. He said he doesnt have any feelings for her yet as he strongly believes friendship as the foundation of a relationship so he wants to build that with her first. I actually started feeling upset and sad

recently because of that which made me thinking if I should just let him know that I like him more than a friend.

 

My biggest worry is that he doesn't feel the same way about me and it will jeopardise everything we have. And mostly because we have so many mutual friends, it will also make things very awkward and possibly losing not just him as a good friend but cause a rift among everyone too.

 

I am not sure what to do and how I even approach this. :(

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It's always a risk to hit on a friend. If this guy has never given you any vibe that he is attracted to you then I'm not sure if you should say anything. I've had guy friends that strictly platonic without a hint of any romantic interest coming from either one of us, but I've also had platonic male friends who were clearly attracted to me as more than a friend even though some of them never outright said so. When someone is interested in you as more than a friend you can see it.

 

Besides it is rather odd for someone his age to have never had a gf just because they work a ton. Whoever does become his first gf is going to have a tough row to hoe as he is probably very stunted when it comes to having relationships.

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Yes I think issue is I can’t tell if he is interested in me more than a friend because I am his only closest female friend so he is more open and treats me differently to all our other female friends. I think would javs been easier if I could tell.

 

I used to have a crush on a friend a few years back but I knew he wasn’t intersted in me romantically even though we talked a lot of about things we hadn’t told anyone else. I never said/did anything to jeopardise that friendship. I grew out of that crush and we did become really good friends (he’s moved countries now).

 

In this case I can’t tell at all and I know it’s also more than a ceush I feel for him

Edited by mariababy
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hi mariababy… if a man is 40 or over and never married the chances of him ever getting married is slim to none.

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hi mariababy… if a man is 40 or over and never married the chances of him ever getting married is slim to none.

 

Thanks you are right and that’s pretty helpful. Maybe I will just not say anything and let things work out on its own

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Given his history, I think he's high risk. Yes, he's a workaholic but even workaholics can have relationships if they have the skills and desire to do so.

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If he is 44 and has never had a gf, then there is "something wrong" there, so even if the two of you did get together I guess it would soon become apparent what his real issues are.

He may be "just shy", but that may be the tip of the iceberg...

The chances of him turning in to a regular normal relationship type guy are not high. I guess he is not really a "catch" after all. Leave him to someone else to sort out. Fixer uppers make pretty unsatisfactory partners. At 44 he will not be able to change into who you really want him to be, ie someone "normal".

 

As your whole friendship crowd could be at risk here, I would stay well away.

Cherish and support him as a friend, but do not get involved is my advice.

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Nowhere did OP say she’s hoping to get married with the next guy she meets, so I’m not sure why everyone was warning her about this guy’s long-term potential. Instead of confessing you feelings, OP, perhaps you can start by being a bit flirty with him to test the water.

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Yes as JuneL mentioned, the only reason I mentioned about him not having a girlfriend or being married was to emphasize that he hasn’t had any experience in relationships. I myself have only been in 1 short-term relationship my whole life and we have similar reasons as to why we remained single.

 

He is a close friend of mine and we have travelled many places and I know his family and friends and have seen his “real side” and I know the reasons he remained single so it’s not going to come as a surprise to me.

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hi mariababy… if a man is 40 or over and never married the chances of him ever getting married is slim to none.

 

hmmn does this mean if I am to get married it will have to happen in the next two years then??

 

I am happy single but want to get married,

 

the paradox of life.

 

Yes Maria, I think you need to open the channels a bit here, its worth pushing it a bit perhaps, arrange to go for a few drinks, see if your guy drops his guard a little,

maybe hes holding back from your friend because he really wants you,

 

my view is its worth finding out, let go of the inhibitions

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Foxhall - Yeah already doing that but sometimes like even today he will joke back about marrying each other whereas days like yesterday when he is a little more serious he makies it clear he wont date friends as he doesnt wanna jepordise friendship

 

At the moment I think I might just keep mum and see how things play out

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... when he is a little more serious he makies it clear he wont date friends as he doesnt wanna jepordise friendship

 

That, I guess is a clear signal to you that you are not on his dating radar, else why bring it up?

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emeraldgreen
he strongly believes friendship as the foundation of a relationship so he wants to build that with her first.

 

That's a dumbass way to date. No wonder he's single. Get a man with some experience.

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hmmn does this mean if I am to get married it will have to happen in the next two years then??

 

I am happy single but want to get married,

 

the paradox of life.

 

Yes Maria, I think you need to open the channels a bit here, its worth pushing it a bit perhaps, arrange to go for a few drinks, see if your guy drops his guard a little,

maybe hes holding back from your friend because he really wants you,

 

my view is its worth finding out, let go of the inhibitions

 

there are no hard and fast rules, its just a generalization

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