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6 Sound Tips On How To Handle Dating In An Age Gap Relationship (My Personal Advice And Experience)

I am 20 years younger than my boyfriend, and I’ve learned a lot about how to handle an age gap relationship. This makes for some unique relationship conflicts, but we both seem to be up for the challenge.

It also makes for some strange self awareness, and that is what this post is about.

EDIT: I originally posted this in 2013, and we were married in 2015!

And now I’m updating this in 2022, and I’ve continued to learn lessons. Look for updates on this post <3

Dating Someone Older: 3 Things You’ll Notice

20 Years Younger Than My Boyfriend – How to Handle an Age Gap Relationship

#1: Awareness Of My Age

When we started dating, I became hyper aware of my (young) age. Some background…

A long time ago I worked at Curves, a women’s only gym. The older ladies would always remind me of my youth and inexperience.

They would reminisce about their own younger days, how little they knew, how much they changed.

When they were younger, they didn’t know any better. They weren’t aware of their twenty-something-ness when they were in their twenties; but seeing me in their maturity reminded these ladies of themselves.

The thing is, dating someone in an age gap relationship who has this much maturity on me makes me unnervingly aware that I am a twenty-something.

So not only am I stumbling around in the dark trying to find myself, but I am now completely aware that I a stumbling around in the dark trying to find myself…and it is weird.

I know some of my reactions to things are immature.

I know there are things going on in the world that I don’t care about because I’m focused on my twenty-something stuff.

2: Awareness Of My Friendships

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I noticed that many of my friendships lacked the depth I saw in my boyfriend’s friendships. I think this depth comes from age…

I am also more aware of my lack of deep friendships in this age gap relationship with my boyfriend.

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I have a small circle of women I’m close to, an amazingly awesome group of cycling friends, many random friends I met through my boyfriend, and a couple old friends I met through church or school.

Twice now in the past two years, I disconnected from huge groups of people with whom I’d spent most of my social time.

There were reasons for it.

It was painful, but it also led to growth and independence.

Even though the changes were good, starting over socially has meant that my inner circle is small.

My boyfriend has many deep, meaningful, long-term friendships. I admire that.

3: Awareness Of My Career

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I realized how early I feel in my career, and the fact that I wasn’t yet on a clear career path…

I also feel like I am “finding myself” in regards to career, and I think it has to due with being in this age gap relationship.

This year I think I may have found my niche; but its been a journey getting there, and I have a lot to learn.

My guy had a clear vision and passion when he was my age, and he specialized and became really spectacular at something.

I’m still floating around trying to do everything I like, and not really an expert at anything (yet).

The wonderful is being inspired by someone with more life experience.

Most people like to give advice, but it is really nice just to observe and see someone’s experience, then decide what I want for myself.

My Advice For Dating Someone 20 Years Older

I originally wrote this post back in 2013, and as of writing this, we’ve been happily married since 2015.

If you are 20 years younger than your significant other, I definitely have some tips and considerations.

I knew I’d look back on the years during our early dating and roll my eyes at myself.

Just like those women at Curves, I’ll laugh at how seriously I took everything. I’ll also be grateful, though.

All those things turned out to be true.

And with more years of hindsight, experience and wisdom, there are a few questions you should ask yourself before dating or marrying someone with a significant age gap.

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Consider Your Goals.


When marrying or dating in an age gap relationship, I highly recommend considering your long term goals.

For example, while Chris and I can have kids of we wanted to, the big age difference adds complications.

As we are, I’m happy without being a mother and I don’t see that changing.

But that’s a huge consideration.

Consider His Past.

Something you need thing really think about is what exactly is this older man bringing into the relationship.

My boyfriend didn’t have any previous relationships before mine, but there are may older men who have had kids in the past.

Are you willing to take on part of his past, even if that means that his kids could be close your age?

I didn’t personally have to worry about this, but I was willing to take that on, if I had to.

Just like any relationship, you’ll have to take on everything in his past – closure from previous relationships, his trials, successes, failures, and everything that happened in that 20 year gap of time difference.

Consider Your Support Network.

This really applies to any relationship, but one thing that made our age gap relationship easier in the beginning was a strong support system.

Our friends were supportive immediately, but family took time to warm up, especially because of previous emotional abuse that had happened.

Additionally, I’m glad I was in therapy at the time we started dating.

There is a lot of stigma around age gap relationships, and I liked having a professional to hear my speak and give me feedback.

I wanted to make sure my own intentions were good ones, and I wanted accountability in regards to how the relationship was going over all.

I’m glad I had that support. And really, I think having a mentor in your twenties is a game changer anyway.

Are You Okay With Feeling Immature At Times?

One thing I struggled with sometimes was feeling just how mature my older boyfriend was.

While I’m glad that I have an older man who is mature, there were many times in the relationship that I felt immature.

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Everything that my boyfriend had experience in the 20 years of difference vastly made him so much more mature that I was.

When I acted my age (a little too immature at times), there was a slight notice of the difference in maturity both of us. My boyfriend was good at not making it as apparent as he could have.

Are you okay with seeing just how immature you can be at your age?

Share Expectations.

Again, this is really important in any relationships, but when you are in an age gap relationship, making expectations clear early on is critical.

The bottom line is that you are both in VERY different phases of life.

Different energy levels, places in your career, levels of debt, savings and retirement, etc.

Get to the bottom of the real life stuff early to avoid frustration later on.

I’ll go ahead and just say it, but sex and money – the two most common struggles in any relationship – are going to be extra for you to talk to your partner about.

Marrying someone older than you might mean different sex drives and different places regarding your money situation.

What do you want and need in the relationship?

Are you willing to be flexible?

Is your partner also willing to compromise and meet in the middle?

60%+ of problems in relationships are NOT resolvable.

So, you’re not looking to avoid problems – you’re getting to the bottom of which issues you can live with, and which you can’t compromise on.

Accepting The Role Of A Caretaker.

This is probably the one I still struggle with the most: when marrying or dating someone significantly older in an age gap relationship, consider care taking roles.

Now, of course I lack the ability for predicting the future.

My husband may end up having to take care of me and not the other way around.

But statistically…you will have to care for your older partner.

Is that something you are willing to do? How can you prepare for it? How can you make sure to care for each other’s health?

Can You Enjoy The Age Difference?

Are You In A Dating Age-gap Relationship?

Have any of you ever dated someone older? Someone younger? What were the challenges? What did you like?

Check out my other article on my relationship advice, where I go into detail on giving you 10 tips for better healthy boundaries in your relationships!

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16 thoughts on “6 Sound Tips On How To Handle Dating In An Age Gap Relationship (My Personal Advice And Experience)”

  1. Alison, You may only be 20 something, but mentally you are light years ahead of most women your age! Love your blog!!

  2. My husband is only 3 years older than I, my contemporary by anybody’s standards. Yet, because of the circumstances under which he grew up and probably by virtue of his strong personality, he has always had a distinct, unwavering sense of purpose since his late teens. I can’t say that he’s wavered more than a smidge our two since I met him when he was 21. Not so for me. I was 30 before I settled in to my life’s work as a calling. Thank God, my dear spouse was enormously supportive and willing to let me find my own niche. So, I’m not so sure all the difference of which you speak are entirely age-related. Much of it is just very typically the stuff of two people coming together and trying to find their way as one.

  3. By the way, this kind of reflection is just what you need to make it work. Great reading!

  4. Chris is a super great guy! Charlie really likes him and enjoys his company! I love Chris to death! In all of your pics together, you always look so happy! I’ve told you this before, that all I really want for my children is to be happy! And you are happy!

    I love you to pieces, Baby Girl!!!!!

  5. My husband is 22 years older than me. To us, it’s completely natural, because we are so much alike and I have always been an “old soul”. I keep him young and he keeps me… mature? LOL Are there difficulties sometimes? Yes. But we’re a perfect match. And that’s really all that matters. It rarely occurs to me that he’s so much older than me. We belong together and we compliment each other perfectly. At the end of the day, age really is nothing but a number. Would this kind of relationship work for everybody? No. It takes the right combination of people. And if you are that right combination, don’t let it go.

  6. Keri, thank you so much for your comment. When my guy and I started dating, our friends told me the same thing: age is just a number. We are so compatible and life is very easy together. Things fell into place so nicely

  7. I stopped here because my fiance is 22 years younger and I’ve never been in such an amazing relationship in my life. We can’t get enough of eachother. She cracks me up and nurture her with care and compassion. We are 4.5 years going unbelievably strong.

  8. You missed the mos important part when strangers ask you “is that your father?”

  9. My boyfriend and I has 22 years age gap. He’s ill-tempered and has mental health issues because of his past. How can I handle that? We’re always having an argument about something even just a small thing. It’s frustrating me.

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