Leon Benjamin
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Leon's Blog


12 Dating Tips to Make it More Meaningful

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Leon Benjamin
·Jun 16, 2022·

2 min read

1. Ask questions about your partner.

Discover their interests. Not just about talking about yourself. You are getting to know them too.

2. Be yourself - this can be the hardest tip of all

This one is challenging since it can be seen as overly confident. But the important thing is to go with the flow. Try to be your best self and honest. The ultimate goal would be that they feel like they can freely express themselves with you without judgement.

3. Share your values and what you’re into

Values go a long way. Tell stories or experiences that can demonstrate these. It can be tiny stories, even about deciding which t-shirt you wore for the date.

4. Three Strikes and move on

If you don’t know where you stand by the 2nd date, ask all your questions on the 3rd date, then make a decision to keep going together or move on.

5. Ask “what does success look like to you?”

See if their response aligns with your values and goals. You can even ask what does retirement look like.

6. Don’t force it, let conversations flow on their own.

Remember that they are getting to know you too. Embrace the present.

7. Give them space to respond.

They don’t owe you any answers quickly or any answers at all.

8. Respect their boundaries

If they state they don't like a certain thing, you don't need to tease them with it over and over. I

9. You are not obligated to respond to them right away either.

Take your time but give them some sort of answer. Do the right thing. Even if it seems difficult.

10. You don’t need to show them all your cards right away.

Some things take time to develop before talking about them. Be patient. Don't rush it.

11. Stay truthful and playful with each other

No need to stay in serious mode all the time. Be playful, yet stay truthful.

12. Be on time, or let them know if you won’t be in advance.

You’ll maintain their trust this way. If you are late and have no explanation, what else would they think about? Would you repeat it in the future? Especially within the first 3 dates. Pay close attention to your punctuality.

Good luck.

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