Am I wasting my time with this guy? 39 year old male, 27 year old female

I'm a 27 year old single, kid free, fun loving gal. He's a 39 year old, annoyingly handsome, wealthy man. Never married,kid free.

So, I met this guy like a year and a half ago at a mutual friends birthday party. We instantly had fireworks, and like 2 hours later we ran into each other upstairs, and passionately kissed for like 2 minutes. We exchanged numbers, and met up for a drink like 2 weeks, followed by like a month or so of steady weekend dates, even had a Christmas eve after-dinner- meet and greet with his dearest friends at a fancy restaurant/bar. We had had a lot of sleep overs but always remained PG, if you know what I mean. After new years, the guy pulls a disappearing act. I see on his Facebook a few months later, that he goes on like once a year, a bunch of pictures with some cheap looking blond with a bad boob job, them on different vaca's etc. This continues throughout most of the year. Whatever. I moved on. I was heartbroken but what can you do.

So flash forward to this past March, and I run in to him for the first time, at some bar. I looked particularly fab that night, good thing. Anyway, we hugged and chatted for like 5 minutes, I even jokingly called him out on his disappearing act, which he apologized for and explained he had a lot going on with his family, etc. Turns out that was the truth! His brother died unexpectedly.. But not until later that year..

Anyway,we have since been back on again..Steady weekly-touch base-communication and Friday night dates fairly regularly. He is still coping with his brothers death and visibly shaken and raw with emotion.(tears still squeeze out when he talks about him)we tried to have sex for the first time and he couldn't keep his sail up. He text me mid April that he "is a f***ing mess and just not there yet..Your amazing blah blah blah" he was drunk when he text this and even followed up with a drunken voice mail repeating this and more tears about his brother. I kept it light and fluffy and said "I understand, blah blah blah, no pressure , we can be movie buddies, I'm hear as sounding board if he ever wanted to talk"

He actually did start to text me or call when he's alone and drunk and sad and we talk about his brother, his feelings etc.

We have since gone on quite a few "buddy" dates and we are getting more and more cozy with each other. regular dinner-movie- sleepovers. We just had our first rated are was good. BUT now he is pulling back I fear: he seemed distant and a bit cocky at breakfast the next morning and I text him Sunday evening and he didn't respond until yesterday(weds)with a call and casual voice mail, which I didn't respond to until today. phone tag.

Bottom line: am I wasting my time with this guy? I'm not tooting my horn but I am a fabulous catch and he knows it. But its hard acting light and fluffy still when I want to marry him and have his babies.hahah. I don't want to push him if he's still shell shocked but I don't want to waste my time! help :(


Most Helpful Guy

  • You're wasting your time. He's emotionally unavailable. And you're being overly romantic about him. It was an impulsive meetup. There was no substance to it. It's more passion than anything meaningful. You don't really know him. You feel this fake connection because he's going through something difficult and you're there. As far as I'm concerned you haven't even met the real him. You've met grieving, vulnerable him. Who knows how long it'll take him to wakeup. Sounds to me like you're the only one putting fourth any effort. So move on, until he's better. Let him come to you, but you move on. Have a little discussion with him about all this before you part ways. So he knows you like him and you're leaving the door open for him.

    • If he were average looking and as broke as the next guy would you still need to ask us? Honestly I question your motivation with this guy. You're into him for the wrong reasons I think. It's just an infatuation with nothing solid behind it.

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    • And NO I'm not after his money. He is super hot and just so happens to be loaded, as well..whats not to love?The fact that he is such a great package makes me insecure, geez, that's all.

    • by the way, that last comment of mine wasn't meant for you.. I responded to the wrong person. ha! you were probably like," weird." lol

What Guys Said 6

  • No you are not wasting your time. Hopefully you aren't just going after him because he's aged gracefully at 40 and he's financially well off.

    The meeting up and making out and seeing you after a couple weeks is cute, makes me feel like things were going well.

    Lots of PG sleep overs makes me feel like you guys spent some time getting to know each other without rushing things. However, I'm hoping you guys at least accomplished some heavy petting, and some make out sessions and foreplay. Because his disappearing act might have to do with that if that whole time he's wining and dining you and you won't even touch his balls...I'd be pissed to and pull a Hoodini as well.

    Also, f*** Facebook. Don't ever use it to stalk guys. So what if he's with some blond bitch on that site, the main concern is why you'd get heart broken and not call him yourself? Girls always do this, they get heart broken for reasons unknown or jump to conclusions and don't make effort to call a guy. THEY WILL DIE ON THE INSIDE WAITING FOR A CALL BUT NOT CALL THEMSELVES. This mis-communication between the sexes screws EVERYTHING UP ALL THE TIME.

    So he tells you his brother died, but you guys pick up right where you left off, which should let you know that disappearing had nothing to do with disinterest with you. It was something else. (Maybe Erectile Dys. and I'd take it at face value if he says he was busy with work and family. He is 39 you know, not some college kid)

    So anyways, I thought this guy was pretty smooth until he pulled the drunken text and phone call. However, telling you he is a mess because of his brother's death though is totally okay, he's obviously devastated over a horrendous lose. Why on earth would you say something like MOVIE BUDDIES? Do you want to give this guy a wrong signal after he tells you that you are amazing? Never keep things "light and fluffy" if someone is going through some trauma in their life.

    So coming out bluntly about his feelings for you and venting over a brother's death and you being kind enough to be understanding might have helped make the next sleepover rated R. Well it was about F***ING TIME. He might have disappeared the first time because everything was so PG and he needs some blond bitch to "release" all his tension. So to speak. Also, the fact that he couldn't get it up at some point might have been the reason he stayed away from you.

    He seemed distant and a bit cocky at breakfast the next morning

    --Not easy for a 40 year old to snag a girl in her 20s.

    I text him Sunday evening. Phone tag

    --He could be playing a little hard to get.

    I wasting my time with this guy?

    --No, but don't let one and a half years slip through by lacking in communication or letting him get distant.

    I'm not tooting my horn?

    --Don't toot your horn!

    But its hard acting light and fluffy

    --Don't act light and fluffy!

    I want to marry him


    Damn, right wen I had advice 4 you I only have 1 character left

    • your rad.

    • i said "movie buddies" right after he told me he was "just not there yet." I was trying to make him feel better by making it 'light and fluffy' and not putting him on the spot you kow? He goes to the movies by himself all the time, and I've always teased him about it..hence, the 'movie buddy' comment.haha I'm not that random. He had the mini mini talk with me last weekend. but now pulling back so I'm like 'wth?'

  • Amazng what women will put up with from a rich guy. Thanks for this page of your diary.

    • have you seen jerry springer, marty? girls will put up a lot more from boys working at home depot or living off unemployement, you barney.

  • I can't be really specific about him since I don't know him, but I'm fairly certain he's not serious about you. You've sent him the message he can pretty much treat you however he likes, so...that doesn't bode well.

    • hmm.. good

      but(!) is it really a lost cause? I know for sure that he is not seeing anyone else.. at least not in public. He does give me what little free time he has. he wakes up at like 330 to be on tokyo time and goes to bed super 830 early, during the week.

      Additionally, I would like to mention I had to put my dog down a few weeks ago and he was super sweet and kept calling to check up on me.. actual calls not texts...

      am I grasping for straws? yikes

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    • yeah, unfortunately, your right. but that's what I've been doing. I keep plenty busy with other boys but I want just him. and now I'm getting impatient. it is what it is I guess. it is summer after all ;) thanks for your input mister. much appreciated.

    • You're welcome.

  • i can't help you because what you wrote here is just your side of the story

    ok I agree that its not nice the way things are going but if he lost his brother and he is still not recovering then maybe you were just a buddy of him who he wanted to share his feelings with and cry

  • So he can't get it up because he is mired in grief and that makes you think you should dump him? Wow, you sound like a real gem.

    • hahaha your funny. No, I really really like this guy but have put myself out there 2x now. And since I really am interested, I'm afraid to get wrapped up in him again and get burned..again.

    • btw, he did get it up last Friday.. my spell check replace the "R" with "are"

  • got one question. If this guy wasn't rich, say average (not poor either) would it impact your attraction to him BE HONEST PLEASE!

    • if he lost everything and had to get a bartending job a cheesecake factory, Id still be his number one fan :)

      He's got that dark irish thing going on...and he came from a super poor background, so he is a hard worker and appreciates how far he has come. the poor upbringing only adds to his charm.. he can be a bit crass at times...i love it. very entertaining fellow :)

    • thanks. Given your response to that I believe you. :)

What Girls Said 1

  • OK... There is nothing you are doing wrong in this situation. You are not wasting your time because a friend is always a good thing to have and you are learning still. If his ding dong is not working properly he is not going to be the most emotionally stable person and is scared of you rejecting him. Older men are more mature and wealthy etc but the non functioning d*** is the drawbavk. Try finding guys that are between the ages of 28 and 32. The blond with the lousy boob job is most probably a skank who knows how to turn older men's d***s so that they feel manlier. Life sucks and us women have to be compassionate with our male partners.