Dear Enchantress,

 Dear Enchantress,

I’m 38 years old and I hate dating. I wish I were better at it. I wish I could have fun. I always feel like I’m interviewing men, like I’m measuring up to something that I think they want, so I do the same to them. I’m doing the best I can. I dress up, I feel good, I think I look good, and I’m tired and frustrated after every date. I meet them on video when we connect and it seems OK, but mostly every time we are just planning our times and dates and locations together. I feel hopeless, and I really want to be in a relationship. I ask nice questions, I’ve read so many books and even when I go on second or third dates, we are sharing stories that I’ve already shared with them, and I’m like, how could that be? We’re already bored and telling each other the same things we’ve already said???!?!?! Please help. 

Dear Boring Betty, 

Ugh, I feel for you. As I read this, I feel the sense of dread you must have, and the exhaustion of getting your hopes up and then feeling dropped into the depths of delusion. OK, let’s lighten up this situation! You can do it. I help so many women that have done it! And I’ll also say, it takes time, practice, and PLAY!  You are acting out of pressure, maybe it’s pressure you are putting on yourself, or pressure that people have put on you. It’s YUCK coming from that place, and putting that on another person will deflate any form of connection or spirit. It’s a spirit squasher, a divine deflator, a BUZZ KILL. You can set your intentions, and you can have your hopes, and that’s it, then show up and be. Stop DOING, stop pressing and stop interviewing. Overshare what is happening for you in the moment with this person. And if you are getting ready for this date, in a logical way, stop that. Instead, when you are getting ready, turn up your music, put on your party shirt and plan on having fun, NO MATTER WHAT.

Learning to turn yourself on is the best skill. You choose the place or the type of place, make it convenient for you, and don’t spend too much time. Plan something that YOU LOVE afterwards, so you don’t let the time drone on. You are a Queen, and you direct your life. Stay just as long as you genuinely want to, and it’s OK to say, “no, thank you” for a second date if you’re just not feeling it!

You can turn this around, and when you feel yourself turning “interviewer” on the person sitting in front of you, tell him that! Tell him so that you can stop it. He may find it funny, or charming, and the best-case scenario, he will find it amazing that you shared it, and POOF, there is the connection and relaxation that always comes right after the spark of connection! Delight yourself Sister, you got this! 

If you want to ask the Enchantress an advice question, email her at

By Shane Kulman

Rockaway Stuff

Related post

Leave a Reply

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