Top 10 Tips for dating a girl ½ your age
Most men — me included – would jump at the chance to date a girl younger than themselves. Some people scoff at the idea (usually middle-aged single women). A feature on my podcast (The SDR Show) is called Dick Tales where we share stories of dating, and a recurring theme is me dating women A LOT younger than me. By the way, let’s be honest – it probably won’t be going anywhere. So don’t kid yourself that she’s the one! She’s not. She’s fun. But she’s most likely not the one — trust me. That being said, here it is my friends – my top 10 tips for dating a girl who you probably shouldn’t date.
1. Keep Current
This is not so simple! But this is the #1 thing for a reason. I keep a top 40 radio station on in the shower, so that every day I hear what new music is out there. We all, at some point, made fun of our parents for not knowing a band, and if your potential playmate says how much she “Loves The Weeknd,” if you respond with “me too, I can’t wait for Friday!” Then you are already done grandpa. Check Reddit, check YouTube, be on top of what’s going on in this new digital age. While you’re at it install Snapchat, WhatsApp or whatever the new app of the moment is… because if a 22-year-old says she wants to kik with you, you better know what that means.
2. Keep it Real, Daddy-O
There’s really no way around it… First and foremost – if she’s obviously A LOT younger, there’s daddy issues there. You know it, I know it. It’s just a matter of fact. But don’t be an idiot about it and ask about her relationship with her father. I assure you it’s not great. If you are in your 40s and she’s in her 20s, she hasn’t written a lot of touching hallmark cards on that third Sunday of June. Last year, I met a gorgeous girl in Texas, after a truly amazing weekend together, she called to tell me her biological father had found her and wanted to re-connect, and as happy as I was for her, I knew it was over for us, and literally the day after she met him, she told me she didn’t think we should see each other anymore. So, right now, take a moment to thank all those absentee dads out there for setting the wheels in motion for you.
3. Keep Her Guessing!
Since you don’t want to answer the question yourself, DO NOT ask her how old she is. DO NOT talk about things that happened to you in the 80s. Always keep it vague. Sentences like “It was a while ago” “back when I was a kid” are fine. “Back in 1989 when I was graduating High School” is a bad idea! I once mentioned to a girl that when I was younger I used to play Ultimate Frisbee with JFK JR, and she paused and said: “Wait a minute?!? You’re over 40?!?” Because she did the math of when he died, and just guessed that I wasn’t 12 playing Frisbee with him, and that ended that night early.
4. Keep Your References In This Decade
Unless she’s a 80s movie buff, there’s no need to talk about how great Caddyshack or The Goonies was. Not to mention how SNL was so much better when John Belushi was on, or how Ronald Reagan was your favorite president. Think about what you are going to say before you say it. That’s simple enough, right?
5. Keep It Mysterious!
Look, I am not advocating lying. I am, however, advocating avoidance. If she asks ‘How old are you?’ Respond with “yes, the lasagna was fantastic” and then excuse yourself to the bathroom, and come back to the table immediately with a new story. If she gets keen to that trick… do the standard “it’s more about how old you feel,” or “what’s in a number?” routine. If she continues to push – my standard response is to give her a 10-15 year span, with my actual age at the end of that span. I’ll say “If you want a number, I am somewhere between 35-45,” Most people wouldn’t think that I am 45 from that statement. Ideally you can keep it vague, at least until you sleep with her once, and then hopefully she won’t care how old you are.
”if your potential playmate says how much she “Loves The Weeknd,” if you respond with “me too, I can’t wait for Friday!” Then you are already done grandpa
6. Keep In Control
One of the charming and attractive things to dating an older man is that you’ve got life experience, and hopefully a few more dollars than she does. So pick the restaurant, send an Uber, talk about the food or the wine or the neighborhood, and show her something that DJ kid with the six-pack abs she used to date would have no idea about. Don’t under-estimate the allure of confidence and experience.
7. Keep It On Your Keyboard
I can honestly tell how old a girl is based on how she likes to communicate. If she’s over 30 she likes talking on the phone. If she’s under – it’ll be texting, Snapchatting, WhatsApp, Kik or Facebook messenger. PLUS – you MUST not use the standard “:)” smiley emoticon. You must use emoji (sparingly). That being said, no twenty-something wants to talk on the phone. It’s a sad state we live in, and eventually all of humanity will have no idea how to communicate face-to-face, but let our great-grandchildren deal with that nightmare, you have this barely legal sex kitten on snapchat right now!
8. Keep Your Energy High
It’s no secret that as we get older our energy depreciates, but if you are going to spend a weekend with a beautiful twenty-something for a weekend, you’re going to have to suck it up my friend. 2-3 years ago, I met a drop dead beautiful woman who worked on a cruise ship – and after texting for a few weeks, I talked her into flying to Vegas with me for the weekend. On my way there, I drank a lot of coffee, and knew I was in for a crazy rough first night. I met her at the hotel, and we both threw our bags in the room and went out until 5am. I never once yawned, complained, said the music was too loud, or asked if she was ready to leave. In fact, she was the one who pooped out before me! I was dying inside… but I always yawned in the opposite direction, and danced till dawn, regardless of my inner misery. The 2nd night she was totally cool with having a more romantic one-on-one evening. So, find your inner 20 year old and let him out for a few hours!
9. Keep It Light
She’s 22! She doesn’t want to hear about your tax problems, or how much your new medication cost, or that you can’t believe you didn’t get that promotion after 10 years at the office! These are old man problems my friend. Your biggest problem is to decide if you are going to Europe or the Hamptons for the summer!
10. Keep It Real!
Of course there are exceptions, but if you’re in your 40s and she’s in her 20s, this probably won’t work long-term, but enjoy it while it lasts! Now go turn on that pop station, download Snapchat and get out there! But you may want to nap first.
You can follow me on twitter/Instagram/facebook all are @iamralphsutton. My podcast is @ www.theSDRshow.com with new episodes every Wednesday, and my radio show The Tour Bus is on 35 radio stations across the country and at www.tourbusradio.com
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Tall in height, short in the pants.
Host of The SDR Show, The Tour Bus, as well as Shiprocked & Motorhead’s Motorboat