10 Great First Date Ideas for Older Men Dating Younger Women

By | July 23, 2017

Let’s set the scene: After weeks of trawling online dating sites in search of a younger woman who prefers older men, you’ve found the ideal lady. She’s young, smart, energetic, and she shares your enthusiasm for age gap dating. You have one opportunity to make a good first impression, so how can you put your best foot forward?

For older men dating younger women, there are some unique obstacles to navigate around that don’t turn up in traditional dating scenarios. Most importantly, there’s the risk that if you aren’t able to keep up with her, she’ll see you as a father figure instead of a potential lover. So how can you show her a great time while also showcasing your vitality and sex appeal? Here are ten first date ideas to help you get the ball rolling. Remember, the key here isn’t to treat her like a child, but to communicate that you’re a youthful free spirit with a strong sense of play.

1. Take her to the zoo

Question: When was the last time you even went to a zoo? Years ago, right? Well, odds are great she hasn’t been to a zoo in ages, either. By suggesting it, you’ll set yourself apart in a good way. Not only will you seem like a fun guy who thinks outside the standard dinner-and-a-movie box, you’ll score bonus points for looking like an animal lover!

2. Picnic at the Park

If the weather’s nice, take her on a picnic at the park. Spread out a blanket, pack a basket lunch and a bottle of your favorite wine. If you’re feeling especially playful, offer to push her on the swings. (Pro tip: Nobody is ever too old to enjoy playing on the swing set!)

3. “Netflix and chill”

Put a fun spin on the traditional “Netflix and chill” by building a pillow fort in your living room. Make a fruit and cheese platter, pour some of your favorite drinks, and cue up a romantic movie. If she feels like cuddling, you’ll be in the perfect position for the “and chill” half of “Netflix and chill.”

4. Photo Booth

Find out whether there’s a photo booth anywhere near you. Grab a pint at your favorite haunt and then commemorate your first date with a keepsake strip of silly souvenir photos.

5. Karaoke

Rent a private room at a karaoke joint and take turns serenading each other. (Warning: Only attempt this one if you can at least carry a tune in a bucket OR you’re prepared to give your wildest, most over-the-top comedic rendition of “Total Eclipse of the Heart” or similar to make her laugh.)

6.  Daddy / Little Girl

This one is special. We know that not all men and women involved in age gap dating are interested in DD/lg (daddy dom/little girl) role play, but if you and your date are then you can’t go wrong with a stuffed animal tea party. Buy her a brand new stuffie to add to her collection, put on your Sunday best, and take your seat at the tea table. You’ll send her straight into little space, and you’ll look like a warm and loving daddy in the process.

7. Try something neither of you have ever done

Try something neither of you have ever done before: Blues dancing? Indoor rock climbing? Sip-and-paint ceramics? The possibilities are endless. Figure out something you’ve both always wanted to try and sign up for it. Getting out of your comfort zone and looking silly in front of each other will help break the ice and start building rapport between you both.

8. Visit a carnival or amusement park

Ride the rides, play some games, and share an elephant ear. Maybe if you’re lucky you can even win her a prize! It’s safe to assume that younger women looking for older men are hoping to be swept off their feet a little bit, and what better way to do that than by scoring a trinket for her?

9. Bar

Attend a bar trivia night together. Have a few rounds of drinks and impress her by showing off your smarts. Even if you don’t win, you can demonstrate your good sportsmanship by accepting it gracefully.

10. Truth or Dare

Play truth or dare. This is a fun, naughty way to learn more about each other and establish a sense of closeness. You could even turn it into a drinking game: If somebody wants to refuse a truth or a dare, they have to take a drink. Whoever finishes their glass first has to buy the next round.

These are only ten potential dates you could go on. The possibilities are only limited by your imagination! If you have any other suggestions you’d like to see listed here, feel free to share them in the comments! What sort of quirky first dates have you been on in your age gap relationship?

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