Top Tips For Dating An Older Man

So, you’ve started dating an older man. You’re head over heels infatuated with each other and having the time of your life; that is until you get to the point where you have to introduce each other to your friends and family. And all of a sudden you find yourself bombarded by questions from different people wanting to know why you’re in this relationship, and it’s so daunting that you have no idea how to answer.

Or: you’re with a group of his (much older) friends and they’re making references to songs or films, or whatever was current in their era, and you start to feel a little bit lost because you’re not really sure what they’re talking about.

The important thing is not to panic – if you don’t want to feel caught out then you just need to do a little homework beforehand. Having always dated older men myself, I’ve gone through this more times than I can count. And over the years I’ve learned a thing or two that I can pass on to you guys here on my blog.

Basically, it all comes down to being prepared. By applying the following 12 techniques your relationship with him will be so much more rewarding. And they’ll most certainly make your life a hell of a lot easier.


Read about the era that your boyfriend grew up in. Google is great for this because there’s a wealth of information at your fingertips. You might even find that you enjoy some of the music or TV shows from those days, so it shouldn’t be that difficult.


Expect some seriously awkward questions and remarks when you first meet each other’s friends and family. You know the ones: ‘Are you after him for his money?’, ‘He’s old enough to be your father’, ‘Do you mind being a trophy girlfriend?’, ‘Have you thought about your future?’ Yadda Yadda Yadda. If you’re prepared for questions like that to come up, they won’t throw you off balance when they do.


Let’s face it, you’re going to be the hot ‘gossip’ for a while. Until some other drama arises that will steal the focus away from you and your man. Try not to get too hurt by people’s comments. They are just trying to deal with it, and they’re doing it in the only way they know how to. Badly.


Write a mission statement (yes I’m deadly serious!) and learn it off by heart, so you can keep repeating it to anyone who asks what it is you see in him. You could say something like you appreciate courtesy and good manners in a man and men of your age don’t seem to have them. Or that you crave the stability that an older man can emotionally offer you. Ha – that’ll stump them! Just don’t joke about only being with him for his money, as his nearest and dearest most definitely won’t see the funny side, and it’s a sure-fire way of rubbing them up the wrong way. And that’s something you most definitely don’t want to happen.


It’s important to remember that he is not alone. He has an ex somewhere, children, perhaps, and most importantly a former life. Get to know his children and listen when he talks about his ex. Don’t try to steal all of his time. If you are prone to jealousy, this is definitely not the type of relationship for you.


Don’t feel like you have to suddenly change your personality to suit his. You guys are together for a reason, and he likes you just the way you are, even if you do feel a little immature at times. Make sure you don’t stop doing the things that you usually do. And be sure to include him in your activities. He’ll be over-the-moon if you do, and it will make him want to get to know you even more.


Older men don’t know anything about the dating games that their younger counterparts seem to have diplomas in these days. It’s a phenomenon that is reserved for the less mature male, so there is no need to start playing games with your new date or expect him to start doing that. He knows what a landline is and he’s not afraid to use it.


Don’t get caught short not having all the essentials that you need for a romantic evening together. If there’s no contraception, there will not be any – and I mean, ANY – sexy time. This is especially true if your man has children already. Create a date night essentials pack, and have it to hand, ‘just in case’. In it, have all the indispensables that you would ever need just in case of things turning – you know – serious. In it, keep stuff like condoms, lubricant, throat spray, etc. Trust me, you’ll be glad you did!


The older the man, the more experiences, relationship problems and arguments he’s most likely had. He’ll have been through lots of breakups and falling outs. In fact, he’s probably had enough experiences to write a book about. Talk about emotional baggage! He probably has a chest or two filled with it. Remember this important information. Why? Well, you know that old saying ‘don’t make the same mistake twice’? This is where he has all of his mistakes stored. Along with all the broken promises, rants, moaning, forgotten dates, lies and cockiness etc. But don’t worry. They are in there safely stored away, never to be used in new relationships.


Being mature, your new man may hold a managerial post, or have his own business. Either way, he has more responsibility at work, and therefore works above and beyond what is normally necessary. Be sure to make allowances for this. Schedule your dates, but don’t fly off the handle if he occasionally has to cancel at the last minute.


Depending on his sense of humour, don’t go on about how wide the age gap is. You can marvel at it from time to time – that’s fine. But if you’re constantly mentioning it, it conveys a message that you think it sucks. It doesn’t matter how much you try to sugar coat it, if you’re repeatedly saying he is an old fogey, he’ll eventually develop a hang-up over it. And, in turn, cause the relationship to go into decline.


Hopefully being mature means he’ll have learnt a thing or two about life and love along the way. This is great as it means that you can learn a lot from him too. And – believe it or not – this works both ways. You’ll be able to teach him a thing or two by looking at problems from a younger perspective.

With so much conspiring against you, you’re probably wondering what makes you so alluring to him? What on earth did he see in you? Well, one of the most obvious answers is youth. Yep – you remind him or his younger, carefree days. But don’t be fooled into thinking that this is the only reason why you guys are dating. He clearly saw something in your personality that drew him to you. Something maybe his friends and family just can’t fathom. They’ll soon come around when they see just how happy you make him. I promise.Top Tips For Dating An Older Man

Have you ever dated an older man before?
If so, let me know in the comments below.

Louise x

Twitter | Facebook | Instagram | Pinterest


  1. May 23, 2020 / 9:04 pm

    I have a few friends that would benefit from this list! I married someone younger than me, and it’s interesting to see the differences between my relationship and your tips for dating an older man. One thing that stays the same is having people talk about your relationship!

  2. May 23, 2020 / 9:10 pm

    Technically I married an older man, lol. Nice tips. Thanks for sharing.

  3. May 23, 2020 / 11:13 pm

    People always talk, but every person needs to do what is good for themselves and whatever makes them happy.

  4. May 24, 2020 / 4:13 am

    I was able to date a guy who was 7 years older than I am before, and I did not know what to do. Sure, he made all of the initiatives, but I was still too immature for the serious commitment that he wanted then. I actually got scared and ran away. I should have read your post earlier than today. Then maybe things would have been different for us.

    • Marta
      May 25, 2020 / 9:09 am

      I married a 7 year older man. Best thing I could have done is to start dating older then my self. He keeps me grounded and understands more then people my age do, especialy when it comes to mental health.

  5. May 24, 2020 / 7:32 am

    I dated an older guy before. What more can I say? Age does not matter, lol.

  6. May 24, 2020 / 11:38 am

    Lovely tips. I will send this article to my sister, she’s been single for a long time.

  7. May 24, 2020 / 2:28 pm

    Interesting read. Dating can be difficult sometimes, so these tips are great for dealing with it, especially where there is an age difference.

  8. May 24, 2020 / 3:03 pm

    Great tips for those who will be in that situation. 🙂 I also love how you emphasized to learn from his/her experiences. Every person we meet always teaches us a lesson. Thank you for sharing!

  9. May 24, 2020 / 4:20 pm

    Wowww, I’ll definitely recommend this to my bunch of friends. I know some of them are into older guys!

  10. May 24, 2020 / 5:47 pm

    it is much helpful for those especially who are dating or who are going to date…it is quite informative….

  11. blair villanueva
    May 25, 2020 / 8:50 am

    Dating an older man is not new to me. I dated a few of them (learned so much from them!) before I finally met my loving partner now. The best part is learning some guidance and tips from them about life decisions making.

  12. May 25, 2020 / 11:58 am

    Dating an older man can be so much fun. When I was younger I dated a man 15 years older than me and I have to say that I’ve learned so much from him.

  13. Harman
    May 25, 2020 / 1:38 pm

    I have always believed that age, race and size is of no use when two genuine people are in love. If i ever date a old man, i now know what to expect and what to be ready for. Do you have any post on inter-caste relationships? I would love to read one.

  14. Chantal
    May 25, 2020 / 3:24 pm

    It is important to do your research. There is a lot that goes into this and you have great tips you are sharing. Awesome post!!!🤗

  15. May 25, 2020 / 5:28 pm

    The one thing I loved the most about dating older men was the fact that they know how to treat a girl right.

  16. May 25, 2020 / 7:25 pm

    These are some great tips but i dont think I could do all that. I dated and older guy without thinking of all this. It didnt work out due him not realizing I was not going to give up my career to move to his country. I might have to take some of the tips into consideration.

  17. May 26, 2020 / 4:43 am

    My man is a whole 11 months older than me, does that count? Haha!

  18. May 26, 2020 / 10:35 am

    I remember I briefly dated a guy who was 14 years older than me and he was talking about going to grad school in the 90’s. This was before we really figured out the age gap. I just remember thinking “wow I was in elementary school then.” We laughed about it later when we were alone. The guy I’m more seriously dating now is only 4 years older than me. These are great tips for someone who more seriously dates an older person.

  19. May 26, 2020 / 4:02 pm

    I haven’t dated an older men however, I am attracted to them because of their wit and perspective in life. And thank you for the tips as it will be handy for me if ever I decided to date a guy 5 or 10 years older than me.

  20. May 26, 2020 / 8:39 pm

    If I was to date an older man,I would never introduce him to anyone.
    That’s just me.
    But great tips, maybe one day these tips will make me change my mind

  21. May 27, 2020 / 12:02 am

    I love the landline reference. I had one until 2009. Got rid of it along with cable! Good luck.

  22. Lavern Moore
    May 27, 2020 / 1:38 am

    Oh wow this is interesting. Never dated an older man but these tips could prove helpful!

  23. May 27, 2020 / 2:00 am

    These are some really great points! Thanks 🙂

  24. May 27, 2020 / 1:59 pm

    I qualify as an older man, and as an older man, I approve of these tips. =)

  25. May 28, 2020 / 7:16 am

    Good tips, expecting questions can help to be prepared and feel relaxed during the discussion.

  26. Elizabeth O
    May 29, 2020 / 2:10 pm

    Very informative post for those who have a May December relationship. I was amused by some comments that saw a 7 year age gap as older, it isn’t. May December relationships tend to be much older 20+ years and I see your post as addressing those type of age gaps.

  27. Maxim Dsouza
    June 15, 2020 / 4:54 pm

    Speaking from a guy’s perspective, accepting a person as the whole package is the most important factor. Seeing things from another’s person’s viewpoint is a key to good relationships.

  28. August 25, 2020 / 9:26 pm

    These are some great tips. The awkward questions are the worst but when you know how to handle them, they can be a breeze.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.