Follow-up Online Dating Message Advice

So, you’ve mined the conversation nuggets from your target’s profile, you’ve sent short, funny, and brilliant one-line hook, and boom, you’ve gotten a response. Now what? This is a very critical point in the online dating process, but this is the final step before meeting in person. This is “the kill,” if you will: the second message with an online dating prospect.

A high-value woman has an incredible volume of messages to manage. The fact you’ve gotten a response speaks to your online dating acumen. But because this woman has such volume to manage, you can’t waste time. You need to meet her as soon as possible. Additionally, you want to ensure that she is who you think she is without investing more time. So, you should have two goals for this online dating message: maintain interest, and secure a date. View Photos of Singles at

First of all, to maintain interest:

  • Build the conversation upon the conversation nuggets you used in your opening message – and those you can find in her response message.
  • Stay playful and funny.
  • Focus on her. Talk as much about interests that concern her as you can.
  • Keep it short: you still have to communicate all of the logistics of a first date in this short message.

Now, for securing the date:

  • Make it convenient for her. Maybe you’ve already learned what neighborhood she lives or works in, or her favorite bar or restaurant. Pick a place that is easy and comfortable for her to get to and be at.
  • Propose a specific day and time. I recommend NOT picking a Friday or Saturday night. That’s valuable social real-estate, and if you don’t have it booked already – a beautiful woman does.
  • Propose 1-2 alternate days/times, to smooth out the logistics of making this date happen. The last thing you want is back-and-forth messages: does this work for you? how about this? no? maybe this? Be a man – be decisive and lead.

As for activity – I think drinks are fine. You get a chance to talk, no distractions. In some cases some common interest (that still allows for first-date conversation) has been mentioned in the opening messages, and is just begging to be the focus of your first date. If this is the case, take advantage.

More specific advice on possible message scenarios can be seen in my post How to Get a Date Online.


  • What do you recommend is the best point to turn to asking to get together for coffee or something else? Is the second third or fourth message appropriate? Seems you might be suggesting second message. I think I have made the mistake of trying to get to know her a little too much over email before asking for a date/meeting…

  • Hey James, I do recommend the second message, but since writing this post, I’ve seen that it kind of depends where you are. In San Francisco, things moved much faster, you had to suggest a meet-up quickly or they would lose interest. In Chicago, a little more conversation takes place before you warm them up enough to want to meet you. That may just be one or two messages more, though.

    The important thing is to keep drilling into the conversation nuggets that are present in the messages so that there becomes such a compelling number of potential conversation threads that they feel like they *have* to meet with you.

  • Hi, I have an interesting question for you. I found a guy on line and added him to my faves and he then added me. So I followed it up with a message; which he took a few days to reply to after reading it. He finally came back asking if I’d like to meet up. Of course I said ‘yes’. He then asked for my number in his 2nd message.. i gave him my number.. that was 3 days ago!! Do I contact him again with a humorous but cheeky reminder? or do I leave it now? :o/

  • Russ Ruggles

    Naomi, sorry for the late reply. I wonder how things turned out. For future reference: I think it wouldn’t hurt to make a nudge like that, but, in my experience, situations like this happen because one person just isn’t “that into” the other. It’s best to strike while the iron is hot.

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