Dear Sasha: Answering Your Most Private Dating Questions – Lonely Guy

  • Posted on: October 10th, 2016 by


Dear Sasha,
I have met a lot of women on various dating apps — but my dates always flop, and I go home feeling sad and lonely. Do you have any tips to help a lonely fella out?

Lonely Guy

Dear Lonely,

You know what sucks about dating?


The sad truth is, 99.9999999999% of your dates are going to be failures.

I know. It burns. But it’ll be okay. It’s not just you, it’s everyone on the planet so take solace in that and try to enjoy the bumpy ass ride.

Here’s my advice to make the whole endeavor more fun:

#1: Take the pressure off.

This is the hardest part. But I swear, if you make it less about “Will this person be my everything? Do they hit every mark on my imaginary checklist? Do I want to spend the rest of my life with them? Do I have something in my teeth? Do they have something in their teeth? What’s that smell?,” you’re gonna have a lot more fun.

#2: Take the pressure off.

I’m serious.

#3: Make the date itself the enjoyable part.

You can’t control your company or whether or not there’s going to be sparks, so make the activity you choose something you’ll enjoy regardless.

Unless you truly loooooove getting coffee and swapping your “I grew up” story, throw that idea in a ditch. So many people are afraid of devoting too much time to a first date in case there isn’t chemistry; don’t be one of those people.

If you’re a foodie, pick a restaurant you’ve been dying to try so you can have a desirable experience while getting to know your date. If you love batting cages and miniature golf, make that the activity. If you’re all about surfing, ask your date to try stand-up paddleboarding. Whatever it is, if you’re in it and will have a blast doing it, not only will your date get to see the real you (which is what they’re going to fall in love with any way), but you’ll have fun too. That way, you may go home lonely, but at least you won’t be sad.

#4: Take the pressure off.

Just let a date be a date. It doesn’t have to be about the rest of your life.

#5: Be interested.

It’s way more important than being interesting.

Everyone wants to feel special and that easiest way to convey that is to listen intently to the person talking. Ask questions, dive deep, find the humor in their jokes, remember tidbits and bring them up later; you’ll score major brownie points.

#6: Don’t be a creep.

If you’re lonely, that probably means it’s been a while since you got any action and you’re a litttttttle horned up. Try to keep that on the QT. Don’t talk about anything overtly sexual or go in for a kiss at the end of the night. Even if there are firework-sized sparks, give a peck on the cheek at most. Leave ‘em wanting more! I’m not saying to slide into the Friend Zone, I’m just saying save it for Date #2.

#7: Take the pressure off.

I know that sometimes it doesn’t feel like it, but eventually you’re going to find someone incredible who loves you just the way you are.

Good luck!

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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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