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Wednesday, June 10, 2026

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Category: Advice

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  • Advice
  • Page 2
  • Advice
  • Matt Kailey

Ask Matt: Correcting Pronouns on Someone Else’s Behalf

  • mkailey
  • September 19, 2013
  • 1

A reader writes: “Our good friends have a daughter, Linda (I changed the name that the reader sent in, because I didn’t know if it […]

  • Advice
  • Laurelai Bailey
  • Opinion

Sometimes it doesn’t get better

  • Guest
  • September 16, 2013
  • 1

Sometimes it doesn’t get better, sometimes life shit on you until you break and there’s nothing you can do. I’m not going to lie to […]

  • Advice
  • Matt Kailey

Ask Matt: What is My Sexual Identity?

  • mkailey
  • September 4, 2013
  • 0

A reader writes: “I am having issues determining my sexual identity since transition from female to male. Dating and having a relationship are things I […]

  • Advice
  • Matt Kailey

Ask Matt: Coming Out at Home and at School

  • mkailey
  • August 30, 2013
  • 0

  A reader writes: “I am a 16-year-old transman. According to my mom, I am much too young to consider myself a transman, and that […]

  • Advice
  • Matt Kailey

Ask Matt: What Am I? Labels and Identities

  • mkailey
  • July 16, 2013
  • 1

Today we have two letters about identity that I thought went together quite well. So here goes: A reader writes: “I consider myself transgender – […]

  • Advice
  • Matt Kailey

Ask Matt: Life Insurance for Trans People

  • mkailey
  • June 1, 2013
  • 4

A reader writes: “I’m curious if, as a trans woman, I would be considered ‘higher risk’ with regard to life insurance than a non-trans woman, […]

  • Advice
  • Matt Kailey

Ask Matt: Do I Owe My Parents Grandchildren?

  • mkailey
  • May 27, 2013
  • 2

A reader writes: “I am a 24-year-old transgender girl. I started transition about a year and a half ago, with one month in between where […]

  • Advice
  • Matt Kailey

Ask Matt: Gender Uncertainty is Stressing Me Out!

  • mkailey
  • May 9, 2013
  • 3

A reader writes: “I’m 18 years old and have lived under the assumption that I was a cisgendered female – identified as lesbian, never really […]

  • Advice
  • Matt Kailey

Ask Matt: On Looking Male

  • mkailey
  • May 2, 2013
  • 1

Today we have a couple of letter related to “male” appearance and expression. I now turn it over to the writers. A reader writes: “I […]

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