Shortcuts: “Should I Have Slept With The Man I Met on Holiday?”

It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences because sometimes the answer to a person’s question is so obvious and the need to hear it so great that being as clear and frank as possible is simply the best way to go.

I am a much older lady, divorced but attractive. I’ve been told not to sleep with men right away, but there was a guy on holiday I fancied who was a similar age and also divorced and whom I regret not sleeping with. I’m sure he wanted to sleep with me, but the holiday was only five days and I don’t jump into bed that quickly as I know that’s a no-no. I don’t get many chances, but I didn’t want him to think I was an easy lay, so what is the answer to that?! — Missed Chance

Screw those dumb “rules”! You’re a grown-ass woman, divorced, and on holiday. If you meet a man you fancy who seems to fancy you, what’s the harm in sleeping together if that’s what you both really want (if you use protection, etc.)? Why would you worry about his thinking you’re an “easy lay”? Would you think the same of him? Obviously not, so why should he think that of you? And of what if he does? It seems that this is someone you don’t have contact with outside of your holiday, so what difference does it make what some guy you’ll probably not see again thinks? If things had gone really well, maybe you’d have kept in touch and made arrangements to meet up again. But instead of pursuing something you really wanted, you let some arbitrary, sexist rule stop you, and it sounds like now you’ve missed an opportunity with someone you may have had a connection with.

After my ex-boyfriend and I broke up, he blocked all my friends on social media and said he was making his social media private because of me, which he did. But he never actually blocked me. I don’t understand why he would block all the girls I know but not me personally. We no longer follow each other on any social media platforms and we have not spoken in three months due to the fact that I found out he was talking to a new girl. I want to eventually reach out to him because I hate the thought of never talking to each other again. Does that make me crazy? What should I do? — Not Blocked

Do not reach out to your ex-boyfriend until the thought of him with a new girlfriend does not bother you, you no longer analyze his social media behavior, and you don’t worry about seeming like a crazy ex. Clearly, you aren’t there yet. Trying to establish some sort of friendship with him before you’re ready will backfire and will increase the likelihood of you two truly never speaking to each other again.

A few days ago I made a joke tinder account with friends, with a fake age, job, etc., but all the pictures were my own. Turns out, I really hit it off with a guy on Tinder and he was still interested after I told him my real information. The thing is, he’s 23 and I’m 17. Is there any hope for a relationship? — Tinder Fake



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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. You are too young, per the guidelines to be on a dating app. A 23 year old who wants to date a high school kid is essentially a predator. Also, stop lying. You could get someone into huge amounts of legal trouble depending on your state.

  2. LW1, in a lot of places age-of-consent laws are strict liability crimes. He could end up on a registry for the rest of his life.

    1. Never mind, reading again I see that he does know how old she is, which makes any possible legal issues his fault. Still, I would stay away from the situation.

  3. anonymousse says:

    Please don’t go out with guys who are okay with dating you, at your age. I know you feel older and mature for your age, but he’s a creep.
    It’s not a rush, trust me. When you are older you will cringe when you think of this. Men who go after girls that are in high school or fresh out of are not good people.

  4. Allornone says:

    Dude, LW3 also wrote to Dear Prudence on April 17th. I guess she thought you might have a different answer. She was wrong.

    1. Allornone says:

      April 12th, I mean

    2. Yes! I thought I saw that somewhere else recently! Why do people do that?!

  5. LisforLeslie says:

    LW 2 – I heard a new term this week “orbiting” to describe when someone with whom you’ve broken up continues to check your social media accounts. It’s like low level non-threatening stalking. Maybe he wants you to orbit. I don’t know. Put this behind you. Don’t check up on him. The relationship is over. Maybe in the future you can find a happy place but right now – no.

  6. The last one has shown up in MULTIPLE advice columns over the past year. I have a feeling it’s some experiment from some weirdo to see what responses it gets.

    1. You can probabky find them by just copy and pasting, they use the same text every time I think.

  7. Allornone says:

    You’re right. as I said above, I saw it on Dear Prudence. It doesn’t surprise me that it’s been submitted to others as well. Weird.

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