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Will dating this older man work out?

Tagged as: Age differences, Dating<< Previous question   Next question >>
Question - (28 November 2004) 10 Answers - (Newest, 24 February 2010)
A , anonymous writes:

I recently met an absolutely amazing guy who I have been seeing for the last 3 months. We have this amazing, open and honest, comfortable relationship. We are both very career minded and busy but always find time for each other. He is charming, intelligent, sweet, fun to be with, and basically an all around perfect guy, except for some small (but significant) details. First of all, we met through work where we technically work for the same company, our office has no policy against this and we do not see each other most days so I don't see this as a major problem, except that my direct supervisor hates him and of course doesn't know I'm seeing him. I think if he found out, I could possibly lose my job. Secondly there is a significant age difference - 16 years (I'm 25, he's 41) is that too much? And lastly, he's just broken up with a serious girlfriend who he admits to me he still loves and says he's devastated by their breakup. In spite of all these things I still want to be with him and he says he wants to be with me too, but he says I'm too young for him and is sure I'm going to leave him any day. Do I work through all these issues, or run away as fast as I can to avoid having my heart broken???

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A female reader, Andonimus United States +, writes (24 February 2010):

Like others have said, you don't need any ex-gf drama. A relationship like this can either continue to go north or head south over his unsure attitude. He went through a bad break up and hopped right into a relationship with you. Are you the rebound girl till his ex comes around? Are you the friend with benefits to make his ex jealous? Or is this a relationship he's looking to build on? This are questions you need to ask yourself before you get your hopes up about having a future with this guy. You're thinking about the risks involved with your job, which I'm glad to hear. So many women don't look before they leap these days and I'm happy to know you're not one of them.

OPEN YOUR EYES! Look for the signs. Ask the trick questions. Find out how he really feels about you. All this "open and honest" behavior is common with people who are feeling vulnerable and depressed. He connected with you during a moment of weakness. When women hit the bottom, we tend to go for the ice cream :( When men hit the bottom, they go for the next vagina.

@ feefeemcgonagle

I read your response and I feel I need to comment. I'm sorry but if an Older Long-time Married Man has 5 children whom he still lives with and plays the part of hubby/daddy while keeping them separate from you, then you're just the BOOTY CALL, and he will say and do WHATEVER it takes to keep you quiet. A relationship that you have to keep a secret from everyone is not a relationship. There's no complicatied misunderstandings about it. Think about it, divorcing his wife and leaving 5 kids behind would financially cripple him in court among other things. The quieter you are about being the "other" woman (and you are), the easier you are for him to drop. Get out while you still can.

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A reader, anonymous, writes (9 December 2008):

Girl I totally understand. I myself am in such a difficult situation. I'm 22 and have been dating a guy who is 37. I met him at work, and we have just clicked ever since we met. However he went to school with my brother and if my brother knew he would want to die, i think.

I am in love with this guy, and we never really talk about it, but if it came down to it, I could spend the rest of my life with him. Hes never been married but does have a child.

However, my family has no clue, and I want to tell them, cuz I don't want to keep it a secret and he does. This makes me feel that if he doesn't want to come out in the open with me then when will he?

Probably like you, I never thought Id be faced with this before. All I can tell you is that you cant help who you love and if its meant to be its meant to be. Age is a number sweetheart, but you have to look more into the ex-girlfriend drama, because that might just cause you hurt in the end. Guys and their exes are unpredictable, especially if they still have feelings for them.

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A female reader, anonymous, writes (1 June 2008):

I am 31 and going out with a man who is 49. We have been going out for just over a year. He is in the process of getting divorced after a marriage of 17 years and has a 18 old son. He is a lovely man, who ticks all the boxes and I love him. However, recently I have been worrying about the age gap, not for now but in later years. He has a lot of work stress and smokes. I am paranoid that in ten years time I could be caring for a sick person or worse still, become a widow. I have always liked older men, as I like wisdom and love the fact they have life experience. Generally speaking, they know how to treat you like a lady too. This is why I think it is a shame that I am so worried about the later years with my partner. Does anyone have any advice on this one?

I sympathize with you and your work situation as I have something similar going on at work, where there is no policy against in work relationships, but my boss is someone who does not condone it. He also happens to be my partner's best friend. Nightmare.

The part about your dilemma that makes me the most concerned for you situation is the fact that he is still getting over his previous partner. For me personally this would be a red warning light to steer well clear. He needs time to sort his head out over this, and should not be playing with your heart until he does so....

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A female reader, feefeemcgonagle Ireland +, writes (30 March 2008):

feefeemcgonagle agony auntFrom reading the other answers and questions i see that you all have been in your relationships for a very short amount of time however still very much in love. I too am seeing a man for 8months and have never felt a love like this before. He is 41 and married with 5 children and i am 21 therefore it is very difficult for people to understand my relationship. My family does not know which is really difficult and my friends dont really take us seriously but i think that these obstacles only make us stronger. He is caring, understanding and i really couldnt imagine life without him. Any worries that i have in my life are completely sorted out by him and i know that if i do get upset about anything that he will immediately make me feel better. im absolutely addicted to his company because he makes me feel beautiful all the time which is usually like pulling teeth with someone ur own age.

Of course there is the jelousy factor as i am young and i would go out more than him but theres always something in a relationship that you have to roll ur eyes at and get through.

Age has never been an issue with him and he has always been supportive of the fact that it would be hard for me to come clean about our relationship.

Depending on your own personality and strengh to deal with this issue will determine your relationship. I am not half as strong as my partner but he builds my strength and it is through his support, understanding and immense love that we have survived.

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A female reader, anonymous, writes (8 February 2008):

we have the same situation but there's some differences too. we are not working in the same company but he is much older than i do i am 27 years old and he is 48 years old when i met him and as well he just broke up with his girlfriend but telling me that he doesnt want to go back with their relationship. it is hard for me because of age gap but when you both really love each other, both of you are willing to adjust. we dated for three months and now im happily married to him. although sometimes he is a typical jealous guy because of age difference but you have to explain to him what your feelings are and sometimes you have to show him how you feel always remember that action speak louder than words. negative consequences and funny part of this is he has a kids almost the same age as me thats why sometimes he thinks that im his kid thats why you have to remind him that im his wife not his kids (LOL!!) eniweyz hope everything turns out between you and him good luck

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A female reader, anonymous, writes (31 December 2007):

My Darling,

Perhaps you ought to be less concerned with your difference in age and more worried about dating a man coming out of a relationship that has left him "devastated". He's obviously showing some insecurities by saying you'll leave him someday. Either he is pushing you away by saying it's because you're too young, or he might still feel wounded by his last relationship and fear something similar happening in a future one.

The best of luck to you.

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A female reader, anonymous, writes (14 August 2007):

hi,am going though some emotional times,but the point is be careful.I have been dating a divorced man of 52 and am 32yrs,we have been together for 1 yr.I recently caught him in bed with a married woman.

So some divorced people dont learn from their mistakes.Just be careful.

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A female reader, chasity81 United States +, writes (18 May 2007):

I am going thru a similar situation. I am dating a 40 year old man and I am 26. He just divorced his wife of 17 years and they have 3 children together. I have 2 children from a privious marriage also. He loves his children and he treats my children no different, however, his ex doesn't want anyone "trying to take her place." As far as our relationship, even if we didn't work out, I wouldn't date anyone else my age. He is a very caring person and he has the life experience that helps me to not "make the same mistakes he did." My ex husband was my age and he was very controlling, very possessive, but I couldn't ever get him to do anything with the family and I wasn't allowed out of the house. My current partner takes everything with ease. He treats me with respect and values my opinion and we actually do things together as a couple and with our children. We have a strong connection and I find it easier to talk to him than I do guys my age. He is a better listener, a better provider and I can actually still have my space without him freaking out. He does voice his opinion on the issue of me maybe leaving him one day when he gets older. The best thing you can do it take each day as it comes and assure him that you view him as a person, not a number and that it would never matter to you how old he is because your choice to be with him had nothing to do with his age, but more his respect for you, for life and for his charming personality :) My partner loves that statement, it always makes him smile. As for the former relationship, you have to realize that this guy does have the life experience and maturity that comes with older age and that he may take his relationships my more serious than guys our age and by that I mean that they actually means something to him, that he was in it for the "real deal" and he recognizes that he still has feeling for his ex, but that doesn't mean that it is a threat to you or your relationship. When my partner and I first got together he was months into a divorce after his wife had an affair after the birth of their third child. He would say things that didn't quite set well with me at first, because he was hurt and it confused me at first. Then I looked back on my failed relationship and thought how it hurt and I told myself that I could just imagine how he feels after 17 years and 3 children and I was in a 4 year marriage with 2 children. It gradually got better the more we seen each other and when we met the others children and things smoothed over in that department. He may care for her, at the same time, that chapter in his life is over and he is moving on. Just be supportive and you will come to find that you actually get closer to him while doing so. He will also get closer to you when he sees that you are there for him and that will make it worth while. I have been dating this guy for almost a year now and the more I get to know him, the more I love him and respect him, as he does me. If it is meant to be, it will turn out in your favor. In closing, older men are much more mature than younger men and they take dating and relationships more seriously. They are actually looking for that person who will stand by them and be there for them and it makes it easier for us to trust them and to be with them when we accept that.

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A female reader, anonymous, writes (14 July 2005):

I think I know what you're going trough. I'm in a practically identical situation. I'm 24 and my partner is 47. We met at work over a year ago.We've been seeing each other for almost 10 months now and I could't imagine a better relationship. We see each other almost every day, at work and private.

Hoewever, the age-difference does bother him. It makes him feel insecure. In his eyes; I am young, with a great future. And although he's very young in his appearance and attitude...i make him feel old...and he's also very affraid that I might leave him when he gets older and older...

But the love is there, my family has accepted him, my friends have as well...

So there's nothing stopping us from making this work, although we feel other insecurities than other couples.But insecurities are always a part of having a relationship. And I think that's also the only option you two have. When you really love oneanother...the age difference doesn't have to be the problem..

From reading your question, I wonder just one thing; is he really over his ex?

And if that turns out to be the real issue...then love just had to it's work...

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A reader, anonymous, writes (2 January 2005):

Actually you both are well over the legal limit. From there age isn't a matter so long as both parties loved one another deeply. He tells you about his recent relationship and etc that proving that he is up front with you and that he is a very deeply romantic person for a girlfriend he had and still deeply in love. He say that you might leave him one day seems that he is insecure the least bit due to his recent breakup problably since he is heart broken after all. A man like him you can't find much these days, a true romantic person. If you can touched him and fill his heart deep enough he would reminisce you the same as to him still sulking about his old relationship. Also touch him with your love so that he would see age is boundless to the feelings you both shared for one another. As for your superior at work, well that including to my final opinion for you is you have to judge if the love is worth it for you to persue. Are you going to choose your job or the love that you would persue for your man. If you choose job then just ignore my advice and leave the guy early on. If you really love him as much then you can even risk it all for him. That is ultimately what love is all about in the end, the risk we take in life.

I hope my advice proves of any use to you and may you find the guiding light for the answers you seek~

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