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Show ALL Forums  > Dating and Love Advice  > Help!!!! My Best Friend's Son Just Asked Me Out      Mod Threads Home login  
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 Author Thread: Help!!!! My Best Friend's Son Just Asked Me Out
 cupidstrikes

Joined: 2/17/2007
Msg: 76
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 2:04:55 AM

I would stick to men closer to your age


How could you say that?
Not all women were meant to be with older men just like not all men were meant to be with younger women.
It's all in the chemistry and how one carries themselves.

I remember when I was 18 and met a 40 yr old offline.
My last g/f is 5 years older (I know that's not that much of an age diff. but it still is one).

Age is nothing but a number. Sometimes you have younger individuals with "older" souls/mentalities/maturity levels.
 CowgirlUp2004

Joined: 1/28/2007
Msg: 77
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 3:15:09 AM

I have always looked at him as "My Best Friend's Son", the thought of him being a love interest never crossed my mind.


Agree with the others that you have answered your own question here.

I just turned 21 a little over a month ago & am nervous about dating a guy that is about 1 year younger than me. I swore NEVER to date a man younger than myself. I can only imagine whats going through your mind being 15 years older. If I were you I'd bring them both into a conversation & explain the devestation that could happen should you actually persue this. I'd rather save a friendship & disapoint a youngster than lose one & live with all sorts of drama. Not to mention your reputation going south VERY quickly.

CG^
 Cheap Trick Fan

Joined: 12/12/2005
Msg: 78
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 9:14:13 AM
To reiterate, the age isn't the worst thing. It's the fact it's your best friend's son. Can you not see how uncomfortable it would be when the two of you break it off, which I would say there's a 99% chance this would not be a "til death do us part" relationship. I would no sooner date my friend's son than I would my supervisor, supervisor's son, or my child's teacher!
 browneyesboo

Joined: 5/19/2005
Msg: 79
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 9:21:27 AM
knock knock! is anyone here?
the issue is NOT the age...the issue is that it is her best friend's son.
I would never feel comfortable with any of my male friends dating
my daughters. I think thats a friendship line you don't cross.
 xssve

Joined: 5/5/2007
Msg: 80
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 9:40:45 AM
It was her friends idea to start with apparently, so it's hard to see it as a betrayal - if this were not the case them I would be less inclined to think it was a good idea if you valued the friendship at all.
 Chippy2

Joined: 6/21/2006
Msg: 81
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 10:07:57 AM
I would say to the gents that say " your best friend`s son, hey go for it"

Think for a minute, how would you feel if your best friend thought of dating, let alone dated and broke the heart of your daughter. Bet you would not be saying "go for it" to him, more like you would want to castrate him.

The fact that the lad`s mum is OK I would like to think he and her have none of the usual hang ups about sex, etc but would wonder.

Age is definately not a concern, hell when I was 35 I dated a woman 9 years older than me. Not a problem you say, definately, it would only have been a problem if I tried to date her when she was 18, afterall I was only 9 then

Age only matters for a short while the gap gets smaller as you both get older, proportionally.

Another thought, your mother-in-law would be your best friend if you went ahead and you stayed together long term, fancy that thought ???????
 lancer5250

Joined: 3/14/2007
Msg: 82
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 3:45:52 PM
If my daughter were 24, I wouldn't have the right to tell her who she could date, and who she couldn't! She'd be a GROWN WOMAN. Capable of making her own choices.

I just don't get this entire thread. Post after post after post of angst-filled, depressing pessimism. What if something bad happened? What if it broke your friendship apart?

Wake up people. Start looking for GOOD things, instead of automatically thinking about the bad ones. That's the reason people fail. They think about failure.

Think about all the happiness, joy, and pleasure the two of them could have, not how much they might damage each other. Sheesh!

I am really wondering about some of these people I've read posts from here...
 SOBEIT19

Joined: 10/15/2006
Msg: 83
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 3:56:27 PM
There is a very fine line we all walk with our friends and family. This is one of them. I have seen some pretty ignorant responses saying go for it, well if you don't value your friendship with your gal pal then by all means do go for it.

There is nothing wrong with dating a younger man, but not your friends son.. It's like taking a shite where you eat..
 Hermia

Joined: 8/13/2006
Msg: 84
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 4:00:49 PM
Good Lord, this woman cannot be serious!
 pouty lips

Joined: 3/6/2007
Msg: 85
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 4:04:42 PM
I feel that any guy in their 20's..who is after an older woman...is only wanting sex.
Just so he can brag to his friends about it later !! In essence, you will be the but of
his jokes. Do'nt be desperate. Only for the fact that is IS your Best Friend's Son...
you best not even do it. How much do you value your "friendship" ?? Obviously,
she is not thinking with a level head. If it were some other 20 +... maybe..just for a
fling. But, she sounds like a screwball. I would NEVER tell me son to go after my
friends. That, to me is morally wrong. I agree with alot of the ladies that said it will
cause chaos. mmhhmm
 Mr.Santiago

Joined: 1/29/2007
Msg: 86
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 4:17:53 PM
You Wrote: What would you do?

I would buy or barrow a camera and post a photo. I have a great deal of trouble believing posts from people without photos. Especially when they are somewhat controversial.
 wanderer1999

Joined: 2/10/2007
Msg: 87
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 5:00:31 PM

There is a very fine line we all walk with our friends and family. This is one of them. I have seen some pretty ignorant responses saying go for it, well if you don't value your friendship with your gal pal then by all means do go for it.

There is nothing wrong with dating a younger man, but not your friends son.. It's like taking a shite where you eat..


Hrm, maybe it's just me, but I've never understood this whole philosophy of "because they're your friend, it's off limits!".

In older days, when towns were smaller and people lived in rural communities, the only people you met to date and marry were the friends and relatives of people you knew... friends of friends, children of friends, parents of friends. It was completely normal, and probably a good thing for people to match make for their friends/relatives, as they knew the characters and personalities of the people who were involved. Even your ex's were nearly always friends of your friends, if not a friend of yours already. And your future dating prospects were the same, friends/relatives of friends or even ex's of your friends.

I've had friends of varying ages, some much younger, some much older, some in my own age bracket. And when any of them tries to set me up with their parents/siblings/friends or children -- I've even had ex's set me up with their friends, I have never been insulted in the least, and actually am flattered. An ex setting you up with a friend is almost the highest compliment there is... as a girl I once knew said, it's like saying, "He's not the one for me, but he's so good I wouldn't want him to go to waste."

I've been in the situation more than once where a person I know says to me, "I wish my daughter/sister/friend/ex met a man more like you instead of the guys that she meeting nowadays...". I took it for what it was, a compliment and sign of respect. In some cases, they were just talking. In other cases, it ended up in introductions, dates, and on one or two occassions real relationships.

In all of those cases, they never ended on bad terms and I still remained friends with my original friends. If anything, I found that I was driven to treat the women better, as I knew that my friend's eyes were upon me, reminding me through their faith in me of the person that I could be.

Similarly, I found that their understanding of both parties meant that problems rarely escalated into significant fights, as they could offer meaningful insight into each person's personality, thus making it easier to address minor issues more easily and more quickly.

I think it's safe to assume that when a friend tries to introduce you to their friend/sibling/parent/child, they are operating upon the assumption that based upon your personality and character as human beings that neither of you is likely to intentionally harm the other in any substantive way. As for accidental heartbreak should the relationship be incompatible, that's a risk of any good relationship... however, I would hope that both parties are mature enough not to hold it against the other if it's discovered that it's just not going to work.

As for the age difference, in many places in the world the age gap is irrelevant. Older men, younger women, older women, younger men, who really cares as long as both people are happy?

In the end, the only real determination that any person can make is what they themselves value and care about.

Not date a friend's ex/friend/sibling/parent? I've trust my friends. The least I can do is give them the benefit of the doubt and see where it leads.

Journey well.
 bucsgirl

Joined: 5/13/2006
Msg: 88
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 5:05:41 PM
There's a reason it's best to avoid dating someone that you have involvement with in other situations. At work (duh) even church (unless you want to find another one) relatives of people you've dated, etc. The reason being that you continue to see these other people and maybe him/her.
It's not what happens if it works out, it's what happens if it doesn't. This particular situation would weird me out to an extreme, just for the fact that if they're as close as me and my sons, it would get very uncomfortable with us still being friends. *shiver*
 cupidstrikes

Joined: 2/17/2007
Msg: 89
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 5:10:35 PM
It's like taking a shite where you eat..




OMFG you people crack me up!

You can't be serious!?

How could you use that as an analogy?

Dating is meant to bring people together and for them to eventually find a suitor/companion.
Dating is supposed to be a good thing, and that's the kind of comparison you make with it?

No wonder you all are alone!





As for

I feel that any guy in their 20's..who is after an older woman...is only wanting sex.
Just so he can brag to his friends about it later


OMG. WTF is wrong with you people?
In some ways I thank God some of you are single because of the negativity/cynicism you all portray!
Who would want others to bring that kind of mentality into their lives?

When I was 25, I dated an older (not THAT much older, but older) woman with a 3 yr old child.
We were together for 2 years, and in many ways she was the one the persued me.
Even as far as sex, it was her that made the first move (after her being impressed that I never made an attempt and she liked to control the pace).
I guess even after playing the role of husband with her and parent to her child I was only after sex.
Even considering that I NEVER hit on her. It was her that made the first sexual move.

*rolls eyes*



In essence, you will be the but of his jokes. Do'nt be desperate.
Only for the fact that is IS your Best Friend's Son...
you best not even do it. How much do you value your "friendship" ?? Obviously,
she is not thinking with a level head.


Why is there desperation there? Here we go with your WINNER (positive) way of thinking again!
You are ASSUMING that it will not work out, and because of that, the friendship MAY be destroyed. Yes, that can very well happen.
OR
It may very well work out. Think of all the younger men that are married to older women. Who's to say that maybe this younger guy may not be the one for her?
Life's full of possibilities and suprises.

There are two types of people in this world
1) The Winners - They are winners in life because even though they have experienced failure(s) they can move on/carry forward and never have to look back at life, wondering "what if?"

THEY TRIED AND NO MATTER WHAT, THEY KEEP TRYING!
This applies EVERYWHERE and with ANYTHING in life.
You can take that to the boardroom, the classroom, work, friendships, romantic relationships, etc.
Thomas Edison failed over 10,000 times. Can you imagine what would have happened if he gave up like the average person would?

2)The Losers - They are the ones that have already accepted defeat. Defeat beat them to the punch. Due to their narrow/closed-mindedness they were defeated in life before they even began because they already think in the back of their minds they are going to fail. With that mentality obvioulsy defeat is what's going to be in-store for them!

But, she sounds like a screwball.

The only screwballs are the number 2's posted above!

I would NEVER tell me son to go after my
friends. That, to me is morally wrong.


And what (how) exactly is morally wrong?
And as far as "telling". I think it was merely a SUGGESTION. I don't think anyone was telling (or forcing) anyone to do anything.
 Real-Me

Joined: 1/12/2007
Msg: 90
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 6:15:59 PM
It's wonderful that Plenty of Fish is a global community more or less but it can make some things confusing.

I think this issue will have a different meaning depending on where you live and what kind of community you surround yourself with.

If you live in a small town or you are sensitive to gossip then the repurcussions of a relationship with your friend's son could make your life uncomfortable.

If you life in a large city where people are open to non-traditional family arrangements, then I think you can easily find acceptance of whatever lifestyle choices you make.

It's interesting that some people who have posted comments believe the fact that you have even brought up this topic means you are uncomfortable with it. To me, if you truly thought this was a no-brainer you wouldn't have brought it up at all or would have portrayed it as a "Can you believe what happened to me?" anecdote that was already over and done with.

If you're considering dating your friend's son and you can live with its aftermath -- whether or not you stay together with him -- then I think you should do it.

I thought the gentleman's story earlier of his relationship with a much older woman was beautifully told and should indicate that you are likely not robbing the cradle or being taken advantage of.

We all bring prejudices to the table based on the standards (or lack of same) of our own communities and upbringings. This thread displays an interesting variety of these prejudices.
 alliealways

Joined: 2/25/2007
Msg: 91
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 6:16:51 PM
I think this is a perfect recipe for "how to lose your best friend".

I pick friends over lovers/dates any day of the week.

Best friends are forever...guys come and go (okay, I KNOW how that sounded...and it's true both ways!)
 This is Now

Joined: 12/4/2006
Msg: 92
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/17/2007 8:32:27 PM
Regardless of whether any relationship that develops between you two lasts two weeks or 20 years, do you really want your best friend for a mother in law? Furthermore, where will you find a shoulder to cry on if he breaks your heart.

Like the saying goes, there are 3 sides to everything: yours, mine, and the truth. And no where does this count more than in break-ups, quarrels, venting about what a jerk he can be at times, how you aren't really sure about a matter and need advice etc.

I can see no winning outcome in this one.
 Cheap Trick Fan

Joined: 12/12/2005
Msg: 93
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 5:41:12 AM
"I found that their understanding of both parties meant that problems rarely escalated into significant fights, as they could offer meaningful insight into each person's personality..."
--------------------------------

That's a nice way of saying that people interfered! That's exactly what happens when you get involved with someone 'close' to you. There's plenty of men out there. She doesn't have to go out with THAT one.
 terry1000

Joined: 3/20/2006
Msg: 94
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 6:05:48 AM
last year when i was 52,i had a couple of young ladies send me letters,27 and 20, that was a big surprice !I never responded to the 27 yr old but i had, to the 20 yr old !I had asked her if she was dylexia where a person see,s words backward, i,m 52 not 25,when you finnish high school ,give me a call !! LOL ! Tell your mother to give me a call ! To even concider dating some one still in colledge at my age is a receipe for DISASTER, not to mention her dad would want to kill me ! Get your hand off your clit and your head out of your ass !!
 craqers

Joined: 10/21/2006
Msg: 95
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 6:21:51 AM
If it never crossed your mind, then why do you even need to ask. Why are you considering it now?

Further more, think about the long term implications.

My gawd, people just don't have any common sense.
 Nick Thinker

Joined: 2/10/2007
Msg: 96
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 6:44:25 AM

I would never feel comfortable with any of my male friends dating
my daughters.


Would one then prefer that one's daughters (or sons) dated not his/her friends but rather, strangers or enemies? What is REALLY wrong with dating?
 browneyesboo

Joined: 5/19/2005
Msg: 97
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Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 7:17:57 AM
^^^ if you check my profile...you would see my age...which would also suggest my friends are around my age. My daughters are in their 20's.
So no...I have friends...and they are just that. I would not feel comfortable with my daughters dating MY friends.
I would prefer that my daughters make their own choices...and since most of my friends are
old enough to be my daughters father or grandfather...I would like to think they could find someone more their contemporaries.
There is nothing wrong with it I suppose...but the question was asked...so I answered.
If my daughters did decide to date my friend...I wouldn't get worked up about it...and I wouldn't suggest it...but it would certainly change the dynamics of my friendship...how could it not?
 Bikeman_

Joined: 10/8/2005
Msg: 98
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 11:38:08 AM
I don't see anything NECESSARILY wrong with the OP's scenario, unlike many folks here making knee-jerk reactions.

Could this scenario blow up in the OP's face? Possibly. Actually, probably. I wouldn't recommend that people look to date their best friend's children necessarily.

OP, if you feel like you couldn't keep your friendship separate from this possible relationship, and vice versa for this dude, I wouldn't pursue it. It would be awkward having normal best friend sex talks with your friend. And you shouldn't be talking about the mom with this guy. He shouldn't be talking about relationship issues with his mom behind your back.

I think it probably won't work; very strange to have a friend recommend that you date their child, but if you can keep things separate, why not go for it?
 SweetCarolin

Joined: 5/9/2007
Msg: 99
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 11:42:28 AM
Oh, good God,...........don't even open that door!!
 E-Grace

Joined: 1/27/2007
Msg: 100
Help!!!! My Best Friend's Son Just Asked Me Out
Posted: 5/18/2007 11:42:31 AM
EW I could never go through with it! I hope you dont! Thats so wrong
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