Unless you are the Goddess of Self Confidence – dating an older man can definitely throw you for a loop.

He’s established and you’re likely on your grind, in process of finding what makes you tick. You’re still figuring things out while he’s been doing his thing for quite some time with a clear idea of where he’s going. You’ve been on a couple dates and the age difference doesn’t seem like a big deal – until it does. There will be an “oh shit” moment – I promise. It might be when he quotes The Andy Griffith Show and you look at him with a blank stare. Or maybe he asks how old your parents are and you realize there is a chance that they all went to high school together. There will undoubtedly be a moment where the age difference hits you. And when that time comes, I encourage you to ask the hard questions.

5 Questions to Ask Yourself Before Seriously Dating an Older Man

Are you established enough to feel confident that he didn’t “make” you?

Alright ladies. Let’s just  get this out there: dating an older, established man means everyone will assume that he’s the reason for your greatness. That’s just a fact. So how does this sit with you? Do you feel you need to prove people wrong? Are you okay with this assumption? I wrested with this one quite a bit. As a young, smart woman, I didn’t want a seat at the table just because Brandon gave it to me. We actually used to fight about this a lot because he’d want me to join business meetings that I had no business being in. I always felt out of place and that I didn’t have anything to contribute but he never saw it this way. I learned invaluable lessons in those meetings but at the time I felt like I needed to contribute something. It’s easy to feel insecure about your place and you just have to be aware on the front end that you might feel this way. If you’re okay with it, there’s nothing to worry about. If you need to prove to people that you can stand on your own two feet without him, I have a couple suggestions:
  1. Don’t work with him
  2. Make your own money
  3. Work hard to create the life you want. The lazier you become, the more insecure you’ll feel.

How do you feel about hanging out with an older crowd?

Friendships can be tricky when you’re dating an older guy, especially couple friends. You likely have your girlfriends and he has his guy friends but I’m willing to bet that the wives of his friends aren’t exactly welcoming of hanging out with someone their daughter’s age and your girlfriend’s guys might look at your guy like a father figure. Yikes! On top of that, if all of your friends are out at the bars while you’re out to dinner with people twice your age, it’s easy to let FOMO creep in. If that’s the case, make it a point to switch things up. If you want to be out with your friends, go do that and get it out of your system. Bonus points if your guy is willing to do it with you. It’s all about balance with this one. We really had a hard time with this at first. My friends were still in college and his were hanging out at country clubs. I felt as if I was living in two different worlds until we made an intentional effort to merge these worlds. He made it a point to connect with my girls and they might even like him more than they like me at this point. His friends have graciously welcomed me into their worlds as well. If you’re feeling a bit like Hannah Montana, there are ways to get creative about how to better integrate your lives as a couple. This takes time but don’t let a little work and patience scare you if you truly adore him and see a future together.

What are your thoughts on having kids?

This is a big one. And my only recommendation is to make sure you’re aligned on this before you make things serious. Bring it up on the third or fourth date at the latest. If you feel one way and he feels another, don’t naïvely think that he’s going to change his mind. This is a clear sign you shouldn’t be together because it will only create resentment down the road and you will have wasted time when the signs were there that it wasn’t going to work from the start. For me, this is a non-negotiable. I’m sure there are success stories out there of people changing their minds and finding happiness. That’s awesome for them. But be smart and listen when he tells you things: even when they’re not what you want to hear. Don’t let your biological clock tick away when you know full well that he doesn’t want kids. Love and appreciate him for the role he’s played in your life and go find someone who shares the same vision for your life as you do.

Is your love worth being alone when he dies?

This can’t be sussed out in the first few dates and will likely take a bit more time to figure out. But let’s not sugar coat this. Statistically speaking, if you are dating a man more than 10 years older than you, he will die 15 years before you as the average life expectancy for women is 81 and men is 76. If this holds true for Brandon and me, I will be 51 when he dies and will have 30 years of life left to live. So the decision I had to make is this: is the love we share for the next 25 years better than the love I could share with someone for the next 50 years? For me, the answer is unequivocally yes. I’d rather have these amazing years with Brandon than be in an average relationship for the rest of my life. Will being alone be painful? Of course it will. But my fear of being alone in the future shouldn’t prevent me from experiencing the greatest love I’ve ever known today. Our relationship is that special to me so it’s worth it. But if you think your guy is a run of the mill, average person to fall in love with, do yourself a favor and find someone closer to your age to have an average relationship with.

Does he compliment the direction you want to take your life?

This starts by knowing what direction you want to take your life. And if you don’t know this, I kindly suggest you figure it out before dating anyone, much less an older man. But once you figure this out, take a good hard look at where you want to go and where he’s going. Do you want to raise a family? Do you want to travel the world? Do you want to have a high-power job? Do you want all of the above? Excellent. How does his lifestyle compliment these dreams? If he wants to travel the world while you want to be in the office 6 days a week, you’re going to have a problem. Similarly, if you want to raise a family and he travels for work incessantly, are you okay with going it alone? It’s not a matter of right or wrong. It’s a matter of understanding how you both want to live your lives and not giving the other one a hard time when they do what they said they would. Alrighty – that’s it for this week.  Who is ready for the weekend?! We have a big birthday weekend ahead. Brandon’s middle daughter is turning 23 today – (Happy birthday Bri!) and tomorrow we are driving down to Bend to celebrate Brandon’s grandson’s birthday. Lot’s of partying happening in the Dawson household. I hope you’re weekend is as eventful as it is relaxing. Until Monday – Xoxo Natalie  


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1 Comment

  1. Katelyn

    I just found your blog, after seeing a post of yours on May December society. I have been appreciating reading your posts about age Gap relationships, as I am currently 4 months into my first one. This post in particular was especially helpful. I definitely had that “oh my God he’s 30 years older than me” moment. For me it was about 3 months in, when he whipped out his phone at dinner to use the flashlight to read his menu. Not a big deal, but I looked over at him and suddenly saw my grandfather, who did the exact same thing. It just hit me in that moment that he is older, and there are things that come with that. I didn’t know if I wanted to/could deal with that. And honestly, 4 months in, I’m in no rush to make things super serious, so I might not be able to deal with the age related asspects. Anyways, thanks for the post, and I will definitely be continuing to stalk you

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