Handle This: Dating Someone 20 Years Older

August 8, 2008

You’ve been close with your best friend since you were kids, and you’ve witnessed her love life every step of the way. After a difficult end to a doomed engagement, she’s been having a hard time moving on.

Next thing you know she’s taken up with a man 20 years older than her. He spoils her rotten, and seems to care about her deeply. You know some people think that age is just a number, but something about their relationship dosen’t sit right with you — from what you know, it seems like he’s made a habit out of dating young women. Now she’s confiding in you that she sees herself marrying him, so how do you handle this?

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37 Comments

2 years 21 weeks

I'm a 37 year old man. I married someone who was 11 years younger then me when I was 33. The road works both ways because my wife left me for a younger guy she met on the internet. I worked really hard to give her everything in life but I was away on business trips and she got lonely...my point here is that young or old both ages know how to cheat and how to be loyal...there are NO RULES in love...Yes, marring someone 20 years older means that you'll most likely be alone during your golden years but if the cards are played right your friend would not have to worry about money and her kids would be set with a gold old fashion life insurance policy...for those who are in a relationship with a significant age gap between - - I would say that it is best that both sides of the fence have a career with some financial security - - that way all you can focus on is love and then marriage...cheers and hats off to those who are loyalists and those who are cheaters - simply be man or woman enough to tell your significant other the truth about your feelings...age - has nothing to do with that...

2 years 39 weeks

well...this is gunna blow your mind. I'm dating a man 35 years older than me. He's great, he treats me right and i couldn't trust someone any more than i trust him. see the heart wants what the heart wants, i can't say that i saw myself with an older man but i love him and his age could never change that. granted he's old enough to be my father but he's not! if your friend wants to be with this man then the best thing to do would be let her. it's her life and if she loves him and wants to be with him then so be it.

2 years 40 weeks

What could a 40yo possibly have in common with a young 20yo who has barely lived? The relationship is one of imbalances,and I think most 40yo men are taking advantage of the young girl's relative naivete. Young girls, don't kid yourself, an older man is skilled at playing romantic games and will -- especially if he is goodlooking and or rich -- almost certainly let you down. Big time!

2 years 42 weeks

i have been recenctly been seeing this guy, i am 21 in sept and he is 45 next month. we have only known each other like 2 days but has been the best 2 days of my life. as soon as we clapped eyes on each other we had a chemisty there, we dint know each others ages at first. wen we found out it was a slight issuse but then we realised the bond and automatic connection we had is far to strong to destroy because of a number. my parents are deffinatly not hung up on the idea but im willing to fight for what i believe in. he has decided to meet my parents and tell them that he is a good guy and wouldnt hurt me. we really like each other and i think we have something big. age doesnt matter one bit as long as he makes her happy. i mean my dad is only 38, hes older than my dad. yeah people are going to talk once it comes out but they will soon find something else to gossip about. just let ya friend know you are there for her and your cool with it. get to know the guy he might turn out to be a really nice chap.

3 years 25 weeks

I'm dating a guy 20 years older we been together for almost two years now. I met him at a restaurant I remember I was waiting to order a drink. He all of sudden turns around and asked me "are you going to order something?". Then the whole entire night there was a spark because we talked all night long until closing time. Then the next day I was looking at his card with his number on it. I asked my friend I met this guy last night and he seem interesting should I call him. She said yeah go for it. So we did meet up and instantly I felt a connection with him. The first year into our relationship was amazing we were inseparable. Now, all of a sudden he tells me he's too old for me. I know some people thinks its gross or not right to date someone old enough to be your father. But I don't think that way because you only live once.If you think that this is what you want. Then whats wrong for us to be together. I know I'm young but I can't help how I feel about this man. He's a great man,loving, caring, takes good care of me. Now, he's pushing me away and its hurting me. Its not the sex its him that I fell in love with. He has my name tatoo on him...what does that mean? Why life have to be so unfair to me?

3 years 27 weeks

I am dating a 49 year old and I am 27. Here is the deal, they can all play mind games as I am sure you can too, there is no connection to their maturity level and it sure doesn't mean they are better in bed. Take it or leave it, and just find your happiness no matter how. You can date any age as long as you are having a good time and it's a mutually respectful thing. Good luck.

ali321 3 years 31 weeks

I don't think age in general should be a problem. If he seems like a bad person that's another story. It depends on the friend. I would hope I would be close enough that I could talk to her about it and let her know I worry. Or at least just discuss the possibility of him growing old way sooner than her. See if she's thought about it. Some people are naive when it comes to love. Unfortunately they usually have to grow out of that themselves. Just be there for her. If handled right there isn't any reason to lose a friendship.

3 years 31 weeks

I am 26 years old and my BF is 20+ my senior. I have been with him for a year now but my family has never met him they know hes older than me. He has been great to me the past year hes so diffrent then all the other boyfriends that i've had that are closer in age to me.

3 years 49 weeks

I'm 48 yrs old, divorced and haven't been asked on a date by ANYONE in at least a year! I and met a 27 year old guy online yesterday who wants to meet me. My first impression was "Geeezzzz! I have a 27 year old daughter!" and I told him that. It didn't deter him at all. He thinks I'm super attractive, he kept saying he wants to get to know the person behind that smile, and I thought...I can either sit here and wait for a guy my age to ask me out, or I can go and meet this guy, enjoy myself (hopefully) and forget about the age difference. Whatever happens, happens.

cloddia 4 years 38 weeks

I'm 18 years old and I'm in a serious relationship with a 38-year old man. I know this is a risky age gap, and I believe that as much as I love him, I remain very watchful of him. For example, does he demonstrate an attraction to younger women in general? Does he buy me things in order to keep me happy? Most importantly, does he expect any sexual favors? Every younger woman dating an older man should make sure of this if they want to move on into marriage.

HonestMuffin 4 years 40 weeks

I have thought about this a lot actually! My 45 year old boss is dating a 25 year old girl, and he has major peter pan syndrome. I would encourage my young friend to think about the future! when you're 50... he'll be 70. Ask her what her parents think?? Does she REALLY love him, and is she not secure in finding someone closer to her age?! What's in it for her, nice gifts? C'mon, lets be honest here!! Who is she fooling! If she's totally fine with changing his diapers, I guess I'd be cool with that.

HonestMuffin 4 years 40 weeks

I have thought about this a lot actually! My 45 year old boss is dating a 25 year old girl, and he has major peter pan syndrome. I would encourage my young friend to think about the future! when you're 50... he'll be 70. Ask her what her parents think?? Does she REALLY love him, and is she not secure in finding someone closer to her age?! What's in it for her, nice gifts? C'mon, lets be honest here!! Who is she fooling!If she's totally fine with changing his diapers, I guess I'd be cool with that.

sldc 4 years 40 weeks

Age can just be a number, but it isn't when a person is attractive to a person because of age. Some men are attracted only to young women and in this case I find it unsettling and shallow. Women are no better when they are looking only at the older man's money. In those situations, eventually, the woman grows older and/or the man grows bored or the woman finds someone with more money. Your friend may not be a shallow sugarbaby, but you should not approach the topic anyway(unless losing the friendship is a risk you are willing to take).

sldc 4 years 40 weeks

Age can just be a number, but it isn't when a person is attractive to a person because of age.Some men are attracted only to young women and in this case I find it unsettling and shallow. Women are no better when they are looking only at the older man's money. In those situations, eventually, the woman grows older and/or the man grows bored or the woman finds someone with more money.Your friend may not be a shallow sugarbaby, but you should not approach the topic anyway(unless losing the friendship is a risk you are willing to take).

Captious 4 years 40 weeks

I'm adopted and have no idea who my biological parents are so I have a strict policy about not dating anyone old enough to potentially be my parent. I won't pester him/her about it but I WILL call their significant other mom/dad. They'll just have to deal w/ it. heh

sundaygreen 4 years 40 weeks

I don't see any of my best friends doing this, and if they did I wouldn't care. One of my friends ONLY dates older men (some of them 60!) because that's just what she's attracted to - who am I to judge (and why would I?)

sparklestar 4 years 40 weeks

Who cares about age? I dated a guy 12 years older than me for 2.5 years and he was wonderful. The age difference was funny sometimes "hey when I started school you were just leaving!" and that kinda thing. ;p It was cool though. As long as you are both mature enough it can work so I would leave her to it!

sparklestar 4 years 40 weeks

Who cares about age? I dated a guy 12 years older than me for 2.5 years and he was wonderful. The age difference was funny sometimes "hey when I started school you were just leaving!" and that kinda thing. ;pIt was cool though. As long as you are both mature enough it can work so I would leave her to it!

RockAndRepublic 4 years 40 weeks

Funny, i just recalled knowing someone that is dating someone 20 yrs + her senior. It's caused some issues with her family so i've asked when she's giving him his walking papers. She too wants it to be over.

ESPNgirl 4 years 40 weeks

Haha, it's like a page out of my life - my best friend IS doing this (however, there wasn't a sad engagement, but a bad break-up). At first, I had a hostile reaction to it - he was married at the time, then he got divorced "because of her," even though he was married for 10 years - but he's growing on everyone and it seems he really cares about her. She is happy, and I am not going to stand in the way of her happiness because there is nothing I wouldn't do for her.

ESPNgirl 4 years 40 weeks

Haha, it's like a page out of my life - my best friend IS doing this (however, there wasn't a sad engagement, but a bad break-up).At first, I had a hostile reaction to it - he was married at the time, then he got divorced "because of her," even though he was married for 10 years - but he's growing on everyone and it seems he really cares about her. She is happy, and I am not going to stand in the way of her happiness because there is nothing I wouldn't do for her.

jessie 4 years 40 weeks

tell her as long as she's happy , go for it!!

rabidmoon 4 years 40 weeks

On the other side of the coin, I am significantly older than my bf, and it works. Its not something I set out to do, I have dated my own age, and older...it just came down to personalities. I don't see him as some sort of "prize", he's just my bf. We get along because we are similar, similar things matter to us, we share music interests, we appreciate what the other one brings to the relationship and we are both very honest. If anything he had to get me to stop worrying about the difference, and I am glad I finally let that go, because it was stupid. Try not to assume the worst, or a stereotype..in the end, it really has to be the person first, not the number over their head.