0119 – Relations Answers Random “When Should I…” Questions


We’ll tell you exactly when you should handle tricky, awkward or embarrassing situations.

By the end of this episode:

  • you’ll learn when you should tell someone you love them
  • when to tell someone their partner is cheating
  • and how to handle other awkward or embarrassing situations

Describe the problem

…We’ve all been there. It’s one of those awkward, tricky or weird situations where we’re not sure if we should say something or make a move. In this episode, we’ll combine our advice with the advice of some of the best experts out there to tell you how to handle some of the most common tricky situations. Stay tuned for more in Episode 119: When Should I…

Segment #1

Note; found these by Google auto-fill when typing “when should I…” and I took the most popular results.


  1. When should I…tell him/her I like/love him? From Psychology Today: “For most regular-looking guys living in places where the desirable women have men quite willing to commit to them, withholding love and commitment might be a formula for celibacy. So better advice to all you regular guys, when you start falling head over heels for a woman, is to go ahead and say “I love you” (but only if you mean it, of course)”
  2. When should I…tell someone I have an STI? From Your Tango: “if you wait too long, your potential partner can feel misled and manipulated. Disclosing early is important (Just don’t make it one of the first conversations you have). As a general guideline, inform your partner before there is any oral-to-genital contact and certainly well before there is any genital-to-genital contact.”

Segment #2

    1. When should I…tell someone their partner is cheating? Do you do what’s right, or what’s good?
  • When should I…tell someone they smell/you can see through their pants/they have something else embarrassing? Anna North on Jezebel recommends:
    • Not “jumping the gun” (wait for a pattern to emerge)
    • Don’t speak out of spite
    • Pick a private space
    • Be clear
    • Let them respond
    • Give space
    • Keep perspective


Final Thoughts:

#1 When considering “when should I” questions, err on the side of what is good and kind. Try to think through what is best for both parties, and what is the kindest way to treat someone else (you know, the way you’d want to be treated).

  • Elijah’s Thoughts
  • Sarah’s Thoughts


In Closing

If you have a question, comment, or funny story about [INSERT SHOW TOPIC] we have a private SafeSpace on facebook where we talk about all sorts of social, professional, and romantic relationship topics, and after every show you can go there and share you story, get some advice from great people or just hang out. Both Sarah and I are there every day and you can be there too, just go to www.relationspodcast.com/join and click the “Join Now’ button.

Until we meet again, keep striving to make every relationship you have the best it can possibly be, including (and especially) the one with yourself. We’ll talk soon.

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