Online Dating – Part Three



Hello, and thanks for visiting my blog today! We conclude this three-part discussion on online dating, where we focus on meeting your match in person. Hopefully, you’ve connected with someone online, exchanged messages back and forth, so now it’s time to go from online to offline. If you haven’t connected with someone yet, no worries. Don’t give up because you are bound to connect with someone, assuming you’ve been putting effort into your initial messages.

And now back to asking that match for a date. Yes, it might seem nerve-racking, but at some point you want to meet that someone you’ve been seeing online in person. Nobody joins a dating site for pen pals, and let’s face it having a pen pal is not going to establish a serious relationship. And just as us guys make the first move in messaging, we’re the ones that ask the girl out (sounds familiar, huh?). While you might be hesitant about meeting a total stranger in person, taking things offline is important for several reasons:

  1. It’s the only way to know if there’s real chemistry. You and her might have great online chemistry, but offline it could be a different story. In fact, you might find that she is not the person you thought you met online. Best to find out sooner rather than later. And at least if it doesn’t work out, you haven’t wasted a lot of time or mental energy.
  2. You are not the only one she is messaging. You can be sure that she is messaging several other guys – and possibly has set up dates with them too. You’ll want to find out there is a potential future with her fast, otherwise someone else will take your place.
  3. It shows you are serious about a relationship. Women don’t like men who play games, and if you hesitate to meet in person she will think you are not serious and move on to another guy.

When should you ask her to meet in person? It depends on the person and the flow of the online conversation. By the time you ask her out, you should know the following about each other:

  • name
  • occupation
  • hometown
  • a little bit about family
  • hobbies

In my experience, I think after five mutual messages it’s safe to take things offline. If you are thinking in days, assuming you have been exchanging messages on a daily basis, I would say go ahead and ask her out after day four. Not sure how to ask her? Try this:

Hey, I’ve really enjoyed getting to know you, and I’m very curious to know what you are like in person. I was wondering if you would like to meet for coffee soon? We could exchange numbers in the meantime. If you’re not ready for this yet, I understand.

This example can’t go wrong. You make the offer, yet acknowledge if she’s not ready to meet you. The worst that can happen is she simply say she’s not ready – yet. Speaking of women not being ready, some women may, in fact, not be as eager to take things offline as you are. Respect this. In this case, just continue to exchange emails. After a week or so, you can ask her out again. Hopefully, by then she’ll say yes. It’s okay if it takes a couple of weeks before you finally meet.

people, lifestyle and dating concept - happy couple drinking cof

So where should you meet for the first time? Some sources will suggest you go all out and have a date filled with multiple activities. Since you’re trying to see if there’s authentic chemistry, a coffee date is the best bet. It’s a public place, relatively quiet, and comfortable, allowing the two of you to get to know each other. It’s just coffee, and if you find there’s no chemistry, you can simply go your separate ways afterwards. When selecting a coffee shop, try and come to a mutual agreement. If she’s like, “I don’t care, you pick,” choose a Mom & Pop type place. Try using Yelp to find the best place, but make sure that it is one that the both of you can easily access and has parking.

Don’t like the idea of coffee? You could go to a bar and have a drink. Just keep the booze to a minimum (for obvious reasons).

Places you SHOULD NOT choose for the first date/meeting:

  • your place, or hers
  • movie theaters (save that for the second, or third date)
  • nightclubs, or any place that’s too dark or loud
  • restaurants (too much potential for disaster, especially when you haven’t met in person yet)

What day is best for the first date? Some sources will tell you to avoid Fridays, Saturdays and Mondays. To be honest, the day of the week makes little difference in whether you’ll have a great time and/or true chemistry. You should choose a day that is good for BOTH OF YOU! And give each other options. Just because you’re free on Sunday, doesn’t mean she is.


What should I wear?
No need for a tux! Just wear something casual, but definitely no lounge wear! Make sure you are cleanly shaven, comb your hair and brush your teeth. Chew on some mint gum half an hour before the date! And ladies, leave the heels at home. Comfortable shoes are a must!

What should we talk about?
Find out more about what you’ve been talking about online. Ask open-ended questions, and avoid the following subjects: politics, exes, religion, and sex.

What if there is true chemistry?
Ask her on a second date, silly! Better yet, take her to another venue such as a comedy club or a walk in the park.

The date was great, but I’m not sure if there is potential. What should I do?
Take some time for thoughts and reflection. It is common for people to be unsure of whether they should see each other again. After a day or two, you will have a better idea. You can either go on a second date, or simply tell her the truth. If you do decide to tell her the truth, do it soon and try and do it over the phone (no texting).

What if I know right away there’s no potential?
You can either ride it out, and mutually part ways after, or lie and say you forgot that you promised to help out a friend (careful with this one since lies end up catching you in the butt). It’s best to be honest in person and end things so as you don’t waste your time – or hers!

Well that wraps up this adventure of online dating. I hope you have learned something from this, and I wish you happy dating! Until next time!

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