Relationship Advice: Dating Older Men

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Dear Guys,

I’m 25 and my boyfriend who I have been with for just over a year is 46. We are in a happy, stable relationship and I noticed him some times whisper, I love you. So I was upfront with him and asked him what he meant. He said he isn’t at that stage yet, and when he does say he loves me it will be because he will be devastated if he lost me. I find I am starting to fall in love with him but don’t want to tell him, so should I wait for him to say that L word? I also would like to have a baby; however he already has two girls and doesn’t want one. Should I stay with him? Should I go?


Dear Amber,

Thanks for your question.

So on the one hand you say he whispers “I love you” and on the other hand you say he isn’t ready to say it. So what’s the deal? Either way his response to your question seems strange. People usually say “I love you” to someone when they have such intense feelings that the words burst right out of them. It sounds like your guy will only say it when he’s about to break up with you.

Let’s focus on something that is clear. Your age difference in itself is not necessarily a problem. (You should listen to our video on Dating Older Men on our video page.) But the problem with such a disparity in age is how it plays out in terms of goals and dreams. You want children. He already has some. You want to get married. He may or may not want to. It’s likely you’re on a different page with every facet of your lives because he’s already experienced many of the things you’re looking forward to.

If you are really serious about this man you need to communicate to him EXACTLY how you’re feeling and what you want out of the relationship—including children. But remember, if he tells you he doesn’t want any more kids after you speak with him again, don’t think you’re going to change his mind. A lot of people stay in relationship thinking, “If this person loves me eventually they will change their mind.” That couldn’t be further from the truth. More typically, resentment builds for both people, and the relationship ends in flames.

We can’t tell you what to do Amber.  But we can say, gather as much information as you can and then make a decision. It’s unlikely he’s going to make the hard decision to break up with you because he’s already getting everything he wants. So it will be up to you to figure it all out.

Good luck,


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4 Comments on Relationship Advice: Dating Older Men

  1. Dear Guys,
    I’m a 17 year old female, I have a part time job, I’m also cosplay model, run my own “budding” Jewelry business, I’m home schooled, and I’m planning on dating a 30 year old male. Yes that is a 12 year difference.
    We met while I was helping two friends of mine who had a booth at a Anime Convention. I saw him in a crowd with a security vest on, and pointed him out to my two friends (both of whom are older and married with teenagers my age) and we all commented on how good looking he was. Later on, when a friend of ours lost a pin she’d just bought. I saw the same guy, thinking he was with con security I asked for his help. We didn’t find the pin, but we did strike up a great conversation. I asked him who he cosplayed as? (Cosplay is a Japanese term combining “costume” and “play”, think of a masquerade ball with VERY elaborate props, minus the ball gowns) I found out that I had seen him at few other Anime Conventions. He told me he was in collage, and asked my age. I coyly replied “A woman never tells her age.” Then my friend came and told me we would be going back to the hotel soon. I said goodbye and turned, but he grasped my hand and asked for my number. I saw no harm in it, thinking he was maybe 23-24. The next day he stopped by the booth and we talked more. His friends came by, we all met and soon we were talking and laughing. His friend Josh made a joke about Corbin being old and grey haired, I laughed and asked how old he was. He replied calmly 29, I was stunned! He laughed at my reaction and asked “Well how old did you think I was”? I told him 23-27 at most. He chuckled, then asked if it bothered me. I said no, but my age might. He looked at my funny, and said you’re what 20-24ish? He guessed up and down, finally I told him I was 17. He thought I was joking at first. He said he would’ve never guessed I was 17. I asked why? He said “It’s because of the way you speak, and how you carry yourself. It says that you’re confident, experienced in the world, and self assured.” We kept it friendly, but there was some playful flirting. We saw each other a few weeks later at a Convention organized party, by the end of the night we knew we were really interested. Despite the age difference, we both wanted to try a relationship. I recently met up with him at another Anime Convention. We were more then happy to see each other, we spent a a lot of time talking, and getting to know each other more. I told him that I had been seriously engaged before I’d met him, he asked me why I decided to get engaged so young? I told him the truth. I’m a logical person, I had known my ex-fiance since I was 7. When he proposed I agreed, I went ahead with my decision realistically. To keep it short, my relationship with my ex was over long before we decided to call it off. My ex admitted he wasn’t mature enough to even to understand how serious that promise was. I’d known that, but I wanted him to realize it. We called it off in February “officially”. Broke up for good in early April. I’d met Corbin in early July. Because of my past relationships I was careful, I didn’t want to rush into anything only to realize that I was rebounding. So I made a promise to myself that I wouldn’t date till after I was 18, settled in what I wanted to do in life, and most importantly when I found someone I felt I could grow with in life.
    Then in walks Corbin, and my “plans” seem like guide lines for a relationship. There’s that old saying that you find love when you least expect it, or when you stop looking for it, seems true, but it seems like it found me instead.
    Corbin and I agreed not to date until after I turned 18, even then, 18 or not he is 12 years older and he wants my parents to be comfortable with him. My parents know the age difference between Corbin and myself, as parents they want to get to know him and more importantly they want me to be careful. He is currently a student professor, teaching Algebra, and taking courses in nano technology about 2 hours away. I keep busy, and like my independence, so the set up at the moment works well for the both of us. We have until late October,(my 18th birthday) to decide if this is what we want and if we can make things work FOR US.
    What makes him different from anyone I met before isn’t the age, (I tend to feel more attracted to older men, I have a lot of good male friends in there late 20’s to 30’s) It’s knowing that I feel secure around him, and I didn’t even realize how secure I felt with him until my mother asked me what made me attracted to him, and what were the feelings I had for him and why? I’ve never felt judged by him because of what I say, how I think, how I dress, or act. Unlike my ex, I’ve never felt like he only bothered to pay attention to me because of my looks. I’ve never once felt like arm candy or some prize to show off, only to put on a shelf when he’s done.
    We’re truthful with each other, I can say that without question or doubt. He’s a responsible, good looking, happy, hard working, successful, independent man, with a beautiful sense of humility towards himself. He was stationed in Korea for 1 year with the Army. Worked in construction, saved up and bought a old home, that he re-built, restored, and lived in until he decided to rent it out to pay for collage. He’s done all this by choice, he wanted to be able to establish financial support for himself so HE could pay for school, and once he graduated he wouldn’t have to worry about scrabbling for a job to pay back loans.
    It’s a long story, but my big question for you Guys is “What advise do you have for this situation?” It’s a strange one indeed, I don’t want to fool myself into thinking I’m mature enough to know everything. There’s plenty to learn in life and a long road a head of me. But life is an adventure of learning, and I’m ready to learn. I don’t think I so nieve in thinking that this couldn’t possibly workout because of the age. Though not so blind to think there won’t be problems along the way. I’m asking you Guys, what should I keep in mind for this relationship and adventure? What sort of advise could you give that might help me better see the road ahead?

    Sincerely~ Misa

  2. I am only a year or so older than you Misa, and I am currently dating a 31 y/o. I will admit there are tough times because of the age difference. mainly from other people who are nosy and judgmental. however, i am so completely happy! you have to make your own decision about whether or not he is too old for you. and further more, your parents need to be aware of your situation.

  3. Stephanie // March 8, 2013 at 8:45 am //

    Hi Guys,

    I recently got engaged to my boyfriend of almost 2 yrs, Carlos (30) I’m 23. He’s divorced and has a two yo son who he sees often, active dad etc. I’ve written in to you about this before. My question is not if I should go ahead with marriage or not, or to run the other way or not. I’m confused about why he out of no where has changed a few weeks after we got engaged. It’s really strange to me, I got with him because he was a little older, seemingly mature, knew what he wanted and had been through marriage before and wouldn’t be scared of commitment. He proposed on valentines day and it was really nice, I accepted and we were excited. Only it seems its all worn off for him and his mood has shifted.. He’s always been expressive, caring, talkative, affectionate – and this got me to open up a lot too and really break my barriers. Now that we’re all engaged and it’s so obvious I love him completely, he’s kinda cold, he’s still nice to me, it’s not enough to cause massive arguments, but he’s distant, and when I bring up conversations about the wedding or baby names (I’m 3mths pregnant btw) he doesn’t seem interested to keep the topic rolling – and it’s its freaking me out to the stage where Ive changed with him too very recently. I try to be colder towards him and protect myself from his indifference so he gets the point that somethings up. He’s not a complete asshole, only different.. and I cant figure out why. He’s been talking about a future together practically since we’ve met… why the sudden change? I get the face that he thinks he can get comfortable from now on, but why… what does that say about his love for me? Thanks

  4. @Stephanie…..We’re sorry. Lots of guys freak out after they get engaged. And it could worsen the closer you come to getting married. You may have been attracted to him because he’s older, more mature, and more experienced, but it’s his experience that we’re somewhat concerned about. In fact, we’re kind of surprised he’s so quick to get back in the marriage game. Most guys who get divorced take a lot of time before they throw their hat in the ring; they throw back many a great lady to continue being single and living life on their own terms. He may be fighting this internally. He knows he’s found a great person, a great partner, a hot lady, but part of him is probably fighting it, the part of him that wants to be free and make up for “lost time.” We can understand why you’re also growing cold but that’s not going to solve anything. Our advice: Get him talking. Suggest couple’s counseling. The two of you need to work this out BEFORE you get married. We urge you strongly to NOT GET MARRIED until this is resolved. You’ll be miserable, and it won’t get better on its own. Hopefully it’s just a phase he’s going through. Keep us posted and take care. Good luck!

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