Ask an Older Guy That Likes You if You Two Are Going Out

Not sure if you can tell your friends that you're "dating" that older guy you went out with? Maybe you need to have a chat with him and find out for yourself first.

Steps

  1. Find a time when the two of you can have a few minutes alone. This may not be the best conversation to have in 30 seconds in a busy school hallway between classes. Whether or not he's not in school with you, try to have this conversation in person so you can better judge his response through body language.
  2. Ask him if he would be interested in going out with you again. This doesn't mean you have to ask him on a date, but it opens up the subject. If he's not interested, that's a pretty solid answer. If he is, you can then approach your next question.
  3. Ask him "So, would you mind if I told my friends that we're dating?" Phrasing it this way shows that you would be pleased to think so, and is flattering to him.
  4. Smile and respond positively to his answers - even if they're not quite what you want to hear. That will increase the chance that he'll be interested in pursuing your relationship further.

Tips

  • When you feel shy, remember that the other person may be feeling shy too. Wouldn't you like them to make the first move?
  • Remember, most older guys (over 40) really like the idea of a younger girlfriend. Also, if he is over 40 and in your school he's probably a teacher and it's illegal for him to date you. Immediately tell your parents if he makes a move on you. You will find something better, I promise.
  • You can talk about anything. Really. Doesn't commit you to do anything. It's all negotiable.

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