online conversation
Dating Advice

Online Conversation: Tips for beginners

Now that you have overcome the initial hurtle of beginning online (or app) dating, have set yourself up with flattering pictures (see Part 1 and Part 2) it’s time to get down to the nitty gritty. Online Conversation.

A lot of people that I know have horror stories from online dating: someone showing up drunk to the first meeting or their date getting drunk on the date, talking about their ex, or wanting the girl to wear a wig that he brought…I have none. Out of all my online dating experience, I had one “crazy” make it through to a short phone conversation. He asked me what I was wearing, got mad when I let him go, and was subsequently blocked. The end.

However, when I first started online dating, I was not so sure of my mad conversation skillz. It was so intimidating. I did not know what to say, or how to say it. I didn’t know if my humor was lost with out vocal intonations and hand gestures. I was worried about keeping someone’s interest, but I was more worried if they were a real person or a cat-fishing scam artist.

This was all part of the process of getting comfortable with online conversations. Until, one day I was comfortable, I was confident and I knew how to hold and direct conversations with strangers to find out if it was someone I wanted to know better.

I attribute my success rate of one “crazy” to two things. 1. I think most people that go online are not crazy. 2. I am really good at vetting people through conversation.

While not everyone we meet might be on our wavelength of normal, we can all work the conversation angle to find out.

online conversation

Here are my online dating conversation tips:

1. Online Conversation: Start with more than hi

Start with a question or remark about one of their photos. Everyone loves to talk about themselves and this is your window to see what type of person they are.

2. Online Conversation: F.O.R.M. them

If conversation does not build from your initial question, FORM them (You can read more about it here.) Ask questions using this acronym:

M-Motivation in life

3. Online Conversation: Get specific

Once conversation is flowing you might want specific information. If you are unsure how to phrase a question, offer information about yourself, followed by a question.


• I have an adorable dog that monopolizes my time. Do you have any pets?
• I work for little known and small division of the IRS representing the people against tyranny. What do you
• I’m an only child. Do you have siblings?

4. Online Conversation: Ask a lot of questions

Use the flow of conversation to get to know about them. Here are some questions that I worked into conversation before I met with someone.

Vetting questions:

Where are they from?
What do they do?
How is their relationship with their mom/ dad/ extended family?
How do they spend their free time?
Do they attend church? What religion are they? How important is spirituality to them?
Do they drink/smoke/do drugs?
Do they have kids?
How long have they been single?
What are they looking for?

5. Online Conversation: Pay attention

Now that you have conversation going:

• If they aren’t responsive or engaging after a few tries, let it go.
• Pay attention to what they say and what they don’t say. Evasive? Brusque? Let it go.
• If you know you have triggers, work it into conversation. Maybe via a story or a polite question
• If they are against meeting in a public place, let it go.
• If they ask or say things that push against your comfort zone, let it go.

Most importantly, be yourself. Speak your mind. Enjoy yourself.

What about you? Do you have any tips to help with online dating or conversations online?

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Article written by:

I love thinking about the intricacies of dating, love and life. I share my tiny lessons in the hope that it helps you as you navigate the dating world.

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