I like a guy, but we can never be

[Alex39]

I started working a new job 4 years ago. I struck up a friendship with a woman in her 60s there and we've been friends ever since. I see her as a mother figure. When she got to know me, she would say how her son and I were so much alike. And she was even hoping he dated me. She gave him my number and he started texting me, just for help getting a job, because I know a lot of people in town.  He and I have been texting on and off for 3 years now. We chat about politics and sometimes other stuff.  He lives with his parents at home. He's 34. But I don't judge him. He was in the military, got out, and then went to college later in life. So he's trying to figure out his career and life.  I know a lot of people so I've tried connecting him and get him jobs. 

My co-worker- his mom and I are very good friends still and she claims that he'd like to take me out but he feels embarrassed and won't because he has nothing to offer me. No money, living with his parents, with nothing. She now says she hopes I meet other more available guys. 

I get his insecurity. I finally met him in-person a few weeks ago. He's everything. He's cute, smart, nice, friendly. 

He's honestly my dream guy. We have so much in common. We even finish each other's sentences. We think the same. It's weird. I really really like him. 

Yesterday I went over their house to help him with some job applications and I stayed all day. I talked with him, his mom, his brother, his dad. It was so comfortable and nice. He and I really hit it off and it felt natural to be around each other, though this was purely professional.  I really like him. 

But he won't ask me out. And I have no idea if he likes me back, though everyone I know thinks he does. But he feels like a failure in life and so unworthy. 

Now, it being the next day, I feel so sad and upset. I got a taste of being around him, but it means nothing, it is nothing. I'm so sad. I feel like it's a cruel trick that life hands me a great guy who I can't have. He still texting me today and he's so nice, but that's all it may ever be. 

 

Even yesterday, I was telling him and his family about how I may want to start up this little at home baking business on the side. And was mentioning the things I plan on baking. And he piped in saying he'd be my first customer. I thought that was cute. 

In the past we've flirted a bit through text, but then it seemed like maybe a joke to him after. So I didn't know if he took it seriously. Then another time he mentioned how he'd be afraid to date me, because he would never want to ruin the friendship I have with his mother. I go out for lunches with her and she and I are close. But his mom used to say she'd love me as a daughter in law. 

I like this guy so so so much, but am I fooling myself? Should I just stop talking to him? Helping him?

I wish we could date. What do I do?

 

[boltnrun]

You're an "NLB". Nice lady, but...

That "but" is key. You're terrific. He knows you're terrific. But that doesn't mean he's interested in dating you.

And that's where your "buts" come in. You can come up with all sorts of ways to excuse or "explain" why he hasn't asked you out. But you're speculating.  You want it to be some external factor, or you want to believe he wants to date you but won't ask because of this or that. But it's all mental gymnastics. He would ask if he wanted to, and why he hasn't is kind of irrelevant because it changes nothing.

If you want, you could throw up a Hail Mary. YOU ask HIM out on a date. Not "want to grab some food?" but "Hey, there's this new movie coming out I really want to see. Would you like to go see this movie with me? And I'd like to take you out to dinner afterward. Are you available this Friday?" If he objects to you buying him dinner you could say "if we have a great time, you can take me out next time." At least that way you'd know if he's interested.

[Wiseman2]

56 minutes ago, Alex39 said:

I wish we could date. What do I do?

Invite him over for dinner. See how that goes rather than everyone else's guessing games. 

[Kwothe28]

Hey, I remember that story. There was also some other woman coworker involved into whole drama as I remember. 

Many years ago, I was that guy. Knew a girl, she was a sister of my friend. She was a really cute architect working at a private firm, full of life, we hanged out, liked to talk about movies(we were both movie buffs), she even had a cute nickname for me. But I also felt inadequate. I was struggling to finish faculty then, and was volunteering with special needs kids for a small pay in local school. So I felt that I have nothing to offer to somebody like that. Who was in the market for somebody to marry her. So I never did anything because of it. Even though she hinted she would like me to ask out. She eventually went out with some lame guy. No higher school education, think he is a physical worker now. He knocked her out and they have a kid now. So after that I promised not to doubt in myself and to pass on opportunities like that. And worked not to feel like I felt then. Actually finished faculty and even got aspiration, tried and managed to get better job opportunities and jobs. Still not perfect but am doing fine at job field right now.

Anyway, I told you this for you to understand that you cant help that guy. If he feels inadequate, he feels inadequate. That is a very tough position to be with, especially maybe for a man. He needs to figure himself out and works on himself. Finish school that he enrolled, get the job, life away from parents etc. And he doesnt seem to do that or trying to work on that at the moment. You know him and message him for 3 years(albeit you met in person few weeks ago so that is pretty weird) and he still didnt worked on anything(you even helped him fill in job applications) to feel adequate enough and gather confidence to even ask you out. He needs to do that work, not you. So his mother is right, you should move on from him and meet other more available guys. At the moment, its your best option.

[boltnrun]

10 minutes ago, Kwothe28 said:

He knocked her out

I hope you meant knocked her "up", not "out"!

[Kwothe28]

6 minutes ago, boltnrun said:

I hope you meant knocked her "up", not "out"!

Yes, my bad. "Knocked her out" would mean that he KOd her like in boxing lol. I meant "made her pregnant". They seem happy though so no hard feelings. 

[SooSad33]

2 hours ago, Alex39 said:

But he feels like a failure in life and so unworthy. 

Do you know this for sure?  I don't know why his parents haven't suggested some prof help if he feels this low about himself? 😕  Do you know if he was affected at all being in the military? 

I get the feeling, IF you were to date, he'd start talking negatively about himself, which would start weighing you down.

For a relationship to be successful, one needs to 'feel good' to extent.  Not sit in a negative.

Does he go out much?  Do anything with others? ( friends etc).  Not sure his lifestyle, but that's something that should do him some good.

I'm sure you've even probably told him that all he's been through & where he is at now, is all okay? That stuff happens in life and is all okay to start again, with new interests & studies.  I went back to college for a study in Healthcare by time I hit my mid 30's.  Didn't feel bad about that at all.

As for you being friends with his mother, I think they've both considered this.  And she's mature enough to have an understanding, should things not work out if you were to date him, your friendship would not change ( hopefully) .. BUT, not sure how it would affect you...

 

[Wiseman2]

2 hours ago, Alex39 said:

I wish we could date. What do I do?

Actually he doesn't fit your requirements/criteria of a guy who is an educated, employed homeowner.

So you could say you're pining or friends, but you  may be so picky that no man will ever be datable in your estimate.

However you could break that fear and mold and invite him for dinner with an open mind.

[boltnrun]

Quoted from your previous thread:

"I want someone with a solid job. I don't care if they are a teacher or a businessman. I don't even care if they went to college, as long as they are pretty financially independent. "

Have you told him these requirements of yours? If so, could that be why he hasn't asked you out?

[Alex39]

2 hours ago, SooSad33 said:

Do you know this for sure?  I don't know why his parents haven't suggested some prof help if he feels this low about himself? 😕  Do you know if he was affected at all being in the military? 

I get the feeling, IF you were to date, he'd start talking negatively about himself, which would start weighing you down.

For a relationship to be successful, one needs to 'feel good' to extent.  Not sit in a negative.

Does he go out much?  Do anything with others? ( friends etc).  Not sure his lifestyle, but that's something that should do him some good.

I'm sure you've even probably told him that all he's been through & where he is at now, is all okay? That stuff happens in life and is all okay to start again, with new interests & studies.  I went back to college for a study in Healthcare by time I hit my mid 30's.  Didn't feel bad about that at all.

As for you being friends with his mother, I think they've both considered this.  And she's mature enough to have an understanding, should things not work out if you were to date him, your friendship would not change ( hopefully) .. BUT, not sure how it would affect you...

 

His mom told me he feels down on himself for being almost 35, living with his parents, no job, no money, wishes he was successful, wants to get married and have kids, but feels so far behind due to his age and placement in life. 

His mom tells me often if how he"@ struggling and keeps getting rejections from jobs and that he won't seriously date anyone because he has nothing good to offer a girl. 

[Alex39]

1 hour ago, boltnrun said:

Quoted from your previous thread:

"I want someone with a solid job. I don't care if they are a teacher or a businessman. I don't even care if they went to college, as long as they are pretty financially independent. "

Have you told him these requirements of yours? If so, could that be why he hasn't asked you out?

I have not told him these requirements.  I do want those things. But I know he will get there. He isn't sitting at home playing video games or being lazy. He goes on interviews and us trying to get jobs. He's smart, doesn't drink, do drugs, he isn't reckless or irresponsible. Just hadn't had good luck with the career thing. 

[SooSad33]

30 minutes ago, Alex39 said:

His mom told me he feels down on himself for being almost 35, living with his parents, no job, no money, wishes he was successful, wants to get married and have kids, but feels so far behind due to his age and placement in life. 

His mom tells me often if how he"@ struggling and keeps getting rejections from jobs and that he won't seriously date anyone because he has nothing good to offer a girl. 

Then maybe it is just best to at least keep it as a friendship, knowing his struggles at this time.  By how I see it, is he's not in the right frame of mind to get involved.. yet... right?

Do YOU think that maybe your paths in your lives are not aligned?  Like, how you're maybe at a comfortable stage ( all okay & ready), but he isn't.  That can cause some issue's. ( Like I said, his mentality, his struggles).

Maybe as you are, at least remain friends with no expectations.  You think that's okay?  I wouldn't want to push anything on someone who's just not themselves.

 

[Batya33]

26 minutes ago, Alex39 said:

I have not told him these requirements.  I do want those things. But I know he will get there. He isn't sitting at home playing video games or being lazy. He goes on interviews and us trying to get jobs. He's smart, doesn't drink, do drugs, he isn't reckless or irresponsible. Just hadn't had good luck with the career thing. 

No this doesn't add up at all.  Luck is a small part of it.  He's got it all cushy at home -does he pay rent? My guess is he has some sort of disorder - or perhaps depression -and they're not sharing this with you.  His parents are enabling this by letting him live at home.  

[boltnrun]

I wonder if people would feel differently if he was female and the OP was male.

A YouTuber I watch worked while her boyfriend went to graduate school. She was the only one working and she supported the both of them financially. She didn't resent him and he didn't feel depressed or inadequate. And according to her no one accused him of freeloading or being a burden or taking advantage of her. They supported one another's goals. And now he's graduated and working and they are doing quite well. 

Of course theirs was an established relationship, not a new dating situation, but still...

[Batya33]

12 minutes ago, boltnrun said:

I wonder if people would feel differently if he was female and the OP was male.

A YouTuber I watch worked while her boyfriend went to graduate school. She was the only one working and she supported the both of them financially. She didn't resent him and he didn't feel depressed or inadequate. And according to her no one accused him of freeloading or being a burden or taking advantage of her. They supported one another's goals. And now he's graduated and working and they are doing quite well. 

Of course theirs was an established relationship, not a new dating situation, but still...

The problem is she says he interviews but this is a long situation and he's living rent free in his 30s so there's some odd dynamic with the parents.  I don't think it is gender based.  My husband would not have dated me were I not in a career I was at least somewhat passionate about.  He asked me this on the first date in 1995.  I know of many men who are apprehensive about someone seeking a man to "provide" for them whether or not they are working in the home raising a child.  

Someone going to grad school hopefully will end up contributing to the couple's income later.  Grad school is working.  Often grad students work part time or are research assistants, etc.  I would never ever have done that outside of a marriage.  I did do it to an extent in my marriage.  My husband attained another grad degree part time over about 5 years.  This meant even more work for him and more travel and less time with us.  He asked me if I would be supportive of this and I said yes. He didn't stop working incredibly hard at his full time job though.  

[SooSad33]

40 minutes ago, boltnrun said:

I wonder if people would feel differently if he was female and the OP was male.

A YouTuber I watch worked while her boyfriend went to graduate school. She was the only one working and she supported the both of them financially. She didn't resent him and he didn't feel depressed or inadequate. And according to her no one accused him of freeloading or being a burden or taking advantage of her. They supported one another's goals.

No.  The issue's I see here is how HE is feeling about himself.  Not the fact on where he's situated at this time.

I also know a few people who have to lean on each other as one goes thru school, etc.

And the issue's the OP is stating. ( His situation and hers and how she see's all of this).

[Andrina]

Do you mean to say that for a whole 3 years since you began texting him he hasn't worked? I know it's possible to not get something in your field for that long, but he should have at least accepted other entry level work outside of his field while still applying for what he wanted. 

It sounds like you're coming out of a desperate state to consider dating someone like this. Good looks and being attractive are only one part of choosing an ideal partner. He's missing financial stability, you cannot determine his work ethic since you haven't seen him work, although you can assume he lacks a good one. Or perhaps his depression is all encompassing and prevents him from being a go-getter, or he sabotages himself for whatever reason.

Basically, he gives more than one reason to not date you.

I'd shove the idea of dating him to the back burner.

If he's really into you, he will work doubly hard to get his life on track so that he will be in a prime place in life to ask you out.

In the meantime, look elsewhere for a prospective partner.

[Alex39]

2 hours ago, SooSad33 said:

Then maybe it is just best to at least keep it as a friendship, knowing his struggles at this time.  By how I see it, is he's not in the right frame of mind to get involved.. yet... right?

Do YOU think that maybe your paths in your lives are not aligned?  Like, how you're maybe at a comfortable stage ( all okay & ready), but he isn't.  That can cause some issue's. ( Like I said, his mentality, his struggles).

Maybe as you are, at least remain friends with no expectations.  You think that's okay?  I wouldn't want to push anything on someone who's just not themselves.

 

I'm not trying to push anything on him at all and would never want to do that. I am okay and I have been okay with being his friend. I think I also have these feelings that I can't get rid of. I wish I could. 

I would never ask him out. I think that would make things very awkward and he'd think I am only helping him find jobs because I like him. 

Yes, half of me is helping him because I like him, half is doing it because I am a nice person and he deserves to be happy. 

[Alex39]

2 hours ago, boltnrun said:

I wonder if people would feel differently if he was female and the OP was male.

A YouTuber I watch worked while her boyfriend went to graduate school. She was the only one working and she supported the both of them financially. She didn't resent him and he didn't feel depressed or inadequate. And according to her no one accused him of freeloading or being a burden or taking advantage of her. They supported one another's goals. And now he's graduated and working and they are doing quite well. 

Of course theirs was an established relationship, not a new dating situation, but still...

I do not at all see him as a freeloader. He feels excessive guilt living with his parents and he genuinely has just had back luck. By the time he left the military he was late 20s, he went straight to college but it was so fast he was unsure what to study, so he just got a basic all around degree. Then after he graduated at 30, he has been struggling to know what kind of job he's qualified for. He's worked on and off and then covid layoffs happened and he's been at an inpass everr since and just lost. So I try to help him. I don't at all think he is a freeloaders or using his parents. He hates that and wants his own place so he can have his own life. 

[Alex39]

50 minutes ago, Andrina said:

Do you mean to say that for a whole 3 years since you began texting him he hasn't worked? I know it's possible to not get something in your field for that long, but he should have at least accepted other entry level work outside of his field while still applying for what he wanted. 

It sounds like you're coming out of a desperate state to consider dating someone like this. Good looks and being attractive are only one part of choosing an ideal partner. He's missing financial stability, you cannot determine his work ethic since you haven't seen him work, although you can assume he lacks a good one. Or perhaps his depression is all encompassing and prevents him from being a go-getter, or he sabotages himself for whatever reason.

Basically, he gives more than one reason to not date you.

I'd shove the idea of dating him to the back burner.

If he's really into you, he will work doubly hard to get his life on track so that he will be in a prime place in life to ask you out.

In the meantime, look elsewhere for a prospective partner.

I do see this. He's been very picky, lost, and determined to work a career or nothing.  He's gone and taken so classes and then stopped them for this reason or another. 

Like in his predicament, I'd work part time at the grocery store until I get act together. His father tells him to just go and work part time until he gets unti a more permanent situation or while he studies for a higher masters degree. But he won't. He's too stuck in his ways. I'm a hard worker and I would have done whatever job I could, if I had no job. 

[boltnrun]

Hmmm...

EVERYONE is hiring. I walk around town and there are signs in the windows in almost every business and companies are posting job listings like crazy.

He doesn't seem to know what he wants to be when he grows up, except he's already supposed to be grown up. Why did he bother getting a degree if not to help him find good employment? And why does a grown man need someone to "help" him find job listings? Does he not have access to the internet?

I think if a man approached you on a dating site or at a party and presented this situation as his credentials you'd decline to date him. But for some reason because this guy is cute and is nice to you he gets a pass?

If he truly wants his own place and his own life he needs to be proactive about it. I'm sure the military has resources to help former service members transition into civilian life. If he's acting passively and waiting for a perfect job he's going to be living with Mom for a long, long time.

[Tinydance]

One thing I think you need to be careful of though is that it sort of sounds like you're trying to get to him through his Mum. Like, you go to their house and hang out with them and you are being egged on by his Mum in terms of something romantic happening between you two. That's great you have a great friendship with his Mum but you are both adults so I think don't involve the Mum in your interactions with him. I think don't talk to her about her son or that you like him and things like that (not saying you have). This isn't like an arranged marriage situation so it's not for the Mum to set you and him up. He should be interested in you on his own so I think leave the up to him.

It's probably normal that he didn't ask you out in the previous three years because you'd never actually met in person. Now that you have met though and spent quite a bit of time together, plus his Mum is trying to matchmake, he still hasn't asked you out. I'm not sure if this is the case but maybe his Mum said all those things like: "He would ask you out but he can't offer much, you should find other guys" to soften the blow because maybe he's not romantically interested? He can still like you as a friend but maybe no more than that.

Having said that, I don't really know why he's not asking you out. He might also be worried that you're his Mum's good friend and if it doesn't work out, things would become very awkward. But still if he really liked you he probably wouldn't want to miss the opportunity to date you, regardless of anything else.

If you really need closure, you could ask him out and see what he says? 

I think you probably need to expand your opportunities to meet other men as well so that you don't just crush on the only guy you talk to. Do you do any online dating? Also joining Meetup groups, singles groups and doing speed dating are good options. 

I would be careful about people in their 30's who ask for help to look for jobs or apply for jobs. Maybe a one off quick help to look at their resume, but not spending all day getting help. This should be something he needs to do on his own. Unless he just used the job help as an excuse to see you or something like that.

Also yeah that's OK if he was in the military and finished university later in life. But being unemployed for three years is too long in my opinion. Some of that was even pre COVID so there should have been job opportunities. If he's been living with his parents and financially supported by them for three years then that's too long.

I think it's also important to note how he goes about his life, career, etc. I don't think it's necessarily a good attitude to be like: "I want a career job or I won't work at all". Especially as he just got a general university degree, I'm guessing like a liberal arts degree? So if his degree isn't really any particular qualification then he needs to either do a Masters degree in an actual profession or some other community college or short course or something. 

I mean, it's good he wants a career but how will he actually get it? Like, what is his plan? Doesn't seem like he actually has one?

Also this is just an offhand comment but I think you need to be mindful of the double standards you seem to have. I remember you very extensively criticising your friend Pam at work because she's 39 and still lives with her Mum, though she does have a full-time job for a number of years. Yet when it's a cute guy your age doing the same (and worse), you don't care and think he's great.

 

[boltnrun]

One more thing...most employers give a side eye to a big gap in employment history. If he graduated more than a couple years ago he should have something on his resume. And the pandemic can't really be used as an excuse anymore. Businesses reopened and people went back to work in mid to late 2020. I got several interviews and started two new jobs during the height of the pandemic, one in fall 2020 and the other in February 2021. So it can be done. But not if you're going to be extremely picky and don't really NEED to work so the urgency isn't there.

[Alex39]

3 hours ago, boltnrun said:

Hmmm...

EVERYONE is hiring. I walk around town and there are signs in the windows in almost every business and companies are posting job listings like crazy.

He doesn't seem to know what he wants to be when he grows up, except he's already supposed to be grown up. Why did he bother getting a degree if not to help him find good employment? And why does a grown man need someone to "help" him find job listings? Does he not have access to the internet?

I think if a man approached you on a dating site or at a party and presented this situation as his credentials you'd decline to date him. But for some reason because this guy is cute and is nice to you he gets a pass?

If he truly wants his own place and his own life he needs to be proactive about it. I'm sure the military has resources to help former service members transition into civilian life. If he's acting passively and waiting for a perfect job he's going to be living with Mom for a long, long time.

I agree wholeheartedly.  He doesn't know what he wants to be when he grows up, but he is grown up. There's his #1 problem. And yes, honestly, if a guy presented himself to me like this, I'd run away. 

I think it's because I've gotten to know his personality and his family, so I have a blind spot and soft spot for him. 

[boltnrun]

It's easy to be sweet and nice when you don't have bills to pay because Mom is paying for everything.

If he truly wanted to get a job and move out he would. Despite his claims, he doesn't seem to want anything to change, not based on what you've written about him. Not even for the chance to date you, unfortunately.

You can have a "soft spot" for him but that doesn't mean he'll transform into a viable dating prospect. He probably knows he can get you to "help" him look for jobs (although I'm not sure what's preventing him from figuring out how to use the internet on his own) and whatever else you're doing for him. I'm sure he can see how you feel about him and he's probably not going to give that up.

But I wouldn't count on him making life changes anytime soon. Unless you're not in any kind of hurry to meet a good man, marry and have children.