Ask Jeff & Anthony

Date but be careful!

Submitted By: Jeff
Date: August 19

In Answer To: Stuck in the Middle (Flat Out Confused)

You don't have an obligation to tell the one person about the other. You're not entering a relationship by going on a date. You can make it clear that you are exploring your interests.

I do suggest you meet each person in a very public place and enforce upon yourself that you will not get beyond a casual, friendly date on the first date. Remember, the internet allows people to misrepresent themselves in any number of ways. You may like a 39 year old, but if he turns out to be 49, you might feel different. Or if the 19 year old is a psychopath, you don't want to be stuck in a place alone with him. Get a chance to know both guys before you make a decision to get intimate with either one.

If you've dated and decided you're going to enter a relationship with one of them, then that's the point that you should worry about creating jealousies.

Questions In This Thread

• Stuck in the Middle
  Flat Out Confused -- August 19
  • Date but be careful!
    Jeff -- August 19
  • Just be Honest
    Anthony -- August 20

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