Amy's Tips For Online Dating

Ever wonder how to go about online dating? What questions to ask to see if it’s a good fit? What steps to take, or when and where to finally meet in person? Here are a few of Amy’s tips on how to navigate the online dating world:

Once you’ve started the opening conversation via chat, begin to ask questions to see if there is a connection. You can even ask if the other person wants to play a “game” - sort of like 21 questions where you both ask answer each one. Make sure the questions really allow both of you to share more details about yourself. You can tailor it to your personal interests, or you can use some of my suggestions:


1. What are you most excited about in life? Where do you feel the most joy/what makes living in this world awesome for you?
2. If you had to describe yourself in three sentences, what would you say?
3. If you had one day to do absolutely anything you wanted - where time/money are not an issue (meaning you could get in a time machine and go/be anywhere) - what would you do? How would you spend it?
4. What is the typical day in the life of being me?
5. Where do I see myself in 1 year? 5 years? 10 years? What are my hopes/dreams?
6. If my therapist were here and they had permission to share what my biggest challenges are in life and/or relating to people, what would they say they might be? (edgy, I know, but let’s just get this one out of the way)
7. The one thing I wish i could change/take back in life is….
8. I am most proud of….
9. My stance on drugs and alcohol is….(edgy again, but why not)
10. My stance on marriage, babies, and monogamy is (by now I think you can handle it).

If it feels like there is a connection via chat or text, feel free to move to a phone of FaceTime conversation. This will help to gauge if the energy is there as chat/text can be limiting. If this feels good, then perhaps it’s time to meet in person. Keep it brief, in public (for safety), and nothing too elaborate. Perhaps starting with getting a cup of coffee, a glass of wine, or going for a walk in a public place.

Bonus tips:

To take the pressure off, go about this with the intention of making a new friend with no expectations. If there is a romantic connection - great! But make that the bonus as opposed to the main goal.

Also, most people are on social media these days, making it easy to learn more about future dates, so feel free to do your research and don’t pretend like that’s not you are doing. Your future date likely did the same.

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