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How Not To Suck At Dating After Fifty

Updated: Jan 16, 2019

Your marriage is over and you’ve been through hell. Now you want to meet someone new but it’s been decades since you went on an actual date and you don’t have a clue about how to approach people online.


Here are a few tips to get you started:


1. Don’t go out there if you’re not ready. We can’t tell you how many people start swiping when they’re not even divorced yet, start messaging prospects long-distance when they have a demanding full-time job and zero ability to get away, or go on dates when their hearts are still broken and all they want to do is rag about how their ex was a total a-hole.

2. Spend some time alone. Even if you hate dining alone and going to therapy, you’ll do everyone a favor if you work on yourself and finish your grieving before you sign up on a dating app.

3. Learn how to flirt again. Flirting is NOT about telling someone you haven’t even met yet that you haven’t had sex in months. And it’s not about jamming your tongue down somebody’s throat on a first date. Eye contact, smiling, listening/asking questions, and being willing to reveal a little bit about yourself instead of spouting off your resume will get you further.

4. It’s not a human smorgasbord. Online dating can be addicting. It can convince you that there’s a never-ending parade of humanity available for you and can make you forget that you’re actually meeting live beings with hang-ups and baggage just like you, and there’s no such thing as a perfect specimen who will inevitably show up if you just keep looking. Unless, of course, you’re perfect and in need of that one other person in the universe just like you.

5. Don’t lie about your age. I know, I know we all feel younger than we probably look, but you’re going to eventually have to come clean and new relationships have ended when the truth comes out, so bite the bullet and say it like it is.


And so much more… like show up on time, quit checking your phone and try to resemble your online photos.


For more ways to not suck at dating, check out my book Secrets of Dating After Fifty: An Insider’s Guide to Finding Love Again





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