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My friend is on a long dating journey. Can I tell her what she needs to hear?

My friend is on a long dating journey. Can I tell her what she needs to hear?


How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous!

Dear How to Do It, 

My friend has been on a long and arduous dating/sexual journey over the last two or so years. It’s really not for the weak out there. It seems like men are increasingly ghosting and even standing people up (with no notice) regularly.

It hurts to see her struggle through this as I know it deeply affects her. She’s vented to me in tears about her latest dating failures many times during this time. There have also been positives! She’s really discovered a lot about what she likes about sex and has explored her interests further in that realm with casual partners.

But lately, she’s had a real string of nasty luck: being stood up, bad dates, mediocre sex, etc. She’s said on more than one occasion that she’s going to go on a dating and sex freeze indefinitely because it’s absorbing too much of her brain space and life… But then like a week later she’s telling me about her latest hookup. How do I support her here? I’m inclined to gently remind her that she thought a break would be best (and from a friend’s perspective, I feel like it could help) but I also don’t want her to ever get the impression that I’m judging her. I just want her to feel good about what she’s doing! How do I navigate this sensitively?

—Stuck Between a Rock and a Hard Place

Dear Stuck,

Your instincts here are spot on. The next time your friend is expressing frustration, remind her that she seems to go back and forth on whether she wants to be dating right now. Listen to what she says from there, and ask clarifying questions to help her think through her situation. If it comes to this point, tell her that you’re worried she’ll think you’re judging her, but that you think a break is in order. Say it clearly, say it once, and then trust that she’s an adult who can make her own decisions.

—Jessica

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