30-Point Online Dating Checklist

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Lately I’ve been thinking about my online dating guide, particularly how it continues to grow and how all the information might be overwhelming to someone new to online dating.

With that in mind, I’ve put together the following checklist that provides dating suggestions at a very high level based on the advice I provide in my dating guide. Where my guide goes into great detail into each area, this list keeps things simple for quick review.

This list is broken down into the major areas of online date: beginning dating online, creating your online dating profile, the communication process, meeting and your first date and, finally, continuing dating online. Each of these sections contains information on how you should approach that phase of online dating. If you are interested in learning more about any of these topics be sure to check out my guide.

Section 1: As You Begin

1. Mentally Prepare Yourself for Real Work
Many believe that online dating will make meeting someone great extremely simple. This is not the case. You will either work at it or you will get lucky. Just because everyone is single doesn’t mean Mr. or Ms. Right is going to fall into your lap.

2. Try the Free Version of Several Sites
Do not choose a dating service based on the commercials you see the most or on what service your friends have used. Sign up for several services and use whatever free options are available to decide what will work best for you. And always use a free service like OkCupid.

3. Be Open to Dating Many People at Once
Why do so many people resist this idea? You need to do this. It is not an issue of quantity vs. quality. It’s an issue of using quantity to find quality. It also helps those new to dating become comfortable, thus reducing nervousness (and bad dates).

Section 2: Your Dating Profile

4. Create a Profile that is Both Concise and Informative
Statements like “I like hanging out” add nothing to your profile. Do not generalize. Describe in detail who you are, what you like and who you are looking for. In this case, it is an issue of quality over quantity.

5. Avoid Excessive Attempts to Be Funny
If you are trying to be funny instead of trying to be informative you will most often be hurting your profile. There will be plenty of time to show your humor once you’ve met. Natural funniness is great but don’t try to prove anything. Avoid sarcasm at all costs.

6. Stay Positive
You need to stay positive in your profile. People love to beat themselves up and say things like “I can’t believe I’m doing this”. Don’t be that person and don’t use your profile as a new way to complain about your life. It is unattractive.

7. Include a Photo in your Dating Profile
You need to have one. You do not necessarily need to show it to the entire world if your service provides options on who can view your photo but you need to have one.

8. Do Not “Beg” For Contact
Do not use comments like these: “If you like my profile please contact me!” or “I’d be totally flattered if you decide to contact me for some reason”. People know how online dating works. Don’t make yourself look desperate by explaining what they should do if they like you.

9. Your Profile Heading
Don’t stress about it. Most profile headings are boring and yet these people are still having success. After all my time dating online, I can’t think of a single profile heading that stood enough for me to remember now.

10. You Need to be Honest
Many people make excuses for “white” lies in their profile. Lying in your profile may help in the short-term but will hurt in the long-term. What good is increasing your number of first dates if they all end there because you lied about your weight, height, age, etc?

11. Check Your Spelling
It seems this should go without saying but log on to your favorite dating site and review some profiles and you will realize it isn’t as obvious as it should be. The one exception would be MySpace where correct spelling is frowned up (Just joking!)

12. Get A Profile Review
Have a friend review your profile, both your text and photos. It is very common for people to use a photo thinking it says one thing about them while it is actually telling a very different story.

Section 3: Communicating

13. Keep Your First Email Short
Sell yourself in your profile, not your first email. The email should just be the tool to show interest and to get your profile viewed. Emails are just profile bait in the beginning.

14. Use Winking Appropriately
Guys, do not wink. Sorry but you need to write emails. I know, life is so unfair. Ladies, you can wink to your heart’s content but you can feel free to email as well. Yes, life is unfair.

15. Respond to Winks Appropriately
Guys: don’t bring up the fact that she winked, just email her if you are interested. Act like you started the conversation. Ladies: if you are fine with taking the lead then email him back. If you prefer your man take the lead just wink back.

16. Accept that Responses Will, at Times, Be Lacking
You send out several emails and get no responses. This is very common and is not grounds to berate yourself. There are many reasons why people do not respond. Concentrate on new people to contact not on people you’ve already contacted.

17. Ask for the First Date Sooner Rather than Later
By the third email an attempt to meet should be made. If you are a woman who prefers to wait for him to ask, you should be offering some encouragement to meet by the third email. You will learn more about someone in the first 10 minutes of a date than you will in weeks of emails, chat sessions or even phone conversations.

18. Seriously, Meeting matters
I just want to reiterate: with online dating your goal is to meet people, not chat with them online. The sooner you meet the sooner you’ll recognize a potentially bad relationship, the quicker you’ll be able to end things with that person. This, in turn, allows you to concentrate of finding the right person.

Section 4: The First Date

19. Keep Your Safety in Mind
Online dating is not dangerous but any situation where you are meeting new people, whether at a bar or online, should be handled with the appropriate amount of caution and intelligence. Think safe, public places and low amounts of alcohol.

20. Review Your Date’s Profile Shortly Before Your Date
Plenty of reasons for this: improve conversations on similar interests, avoid asking questions already answered in the profile, recalling exactly who you’re meeting if you’re dating multiple people, and so on.

21. Schedule Your First Date to be Short
Limit the length of your first date ahead of time. I went with an hour. Explain to your date you’ll only be available for that amount of time. This is protection against bad dates which do happen. This allows you to leave a bad date gracefully.

22. Extend Your Good Dates
Be willing to extend the good dates past the set time. Simply explain to your date that you would prefer to spend more time with them and ask if they have additional time to spend together. What you are telling your date is that things are going great and that you would like to spend more time with them. Delivering this type of message goes over very well and I have seen rather shy dates gain confidence in leaps and bounds just by stating that I would like to extend the date.

23. You Need to be Comfortable
Comfort was the most important factor to my success dating online. Many argue that confidence is the key but for most of us this “confidence” is just an act. Instead, I ensured that I was as comfortable as possible: comfortable with the facts I knew about them, comfortable with where and when we were meeting, etc. My increased comfort led to their increased comfort which led to better first dates.

24. Prepare Your First Date Conversations Ahead of Time
This is not “cheating”. Some people want to rely entirely on chemistry but not every relationship begins with the two of you unable to stop speaking. Sometimes nervousness or hesitation creates a situation where a good conversation is hard to find. Have a script prepared in your mind to help avoid this.

25. Do Not Insist on Sticking with a Script
Preparing a script is a good idea to get the conversation going but should be thrown out when the conversation takes a life of its own. If you stick with a script exclusively you can appear to be putting your date on trial or can appear to be uninterested in what they are sharing. Allow the date conversations to move naturally once you are able to.

Section 5: Continuing to Date Online

26. Be Aware of Online Dating Scams
They do exist and you need to be aware of them. Generally, if money enters the picture (no matter how) you could very well be dealing with a scammer.

27. Share Your Online Dating Experiences with Friends
Don’t bottle everything up. Be open with friends about the frustrations and successes of online dating. Not only can they encourage you, recognizing you are actively dating will cause many people to start trying to find dates for you!

28. Read Additional Advice
I like my advice because it worked so well for me. That said, reading additional advice is always a good idea. What worked for me may not be exactly what works best for you.

29. Be Wary of Advice Too Good to be True
Just like get-rich-quick plans, get-love-fast plans very rarely work. Be wary of advice that makes online dating sound simple but also has a price tag attached to it. Be especially cautious of advice that uses terms like “seduction” overly often.

30. Commit to Your Dating Life
All the advice in the world won’t matter if you don’t keep trying. Commit to date online for a set amount of time and keep your commitment. I would recommend committing to 6 months but you will need to decide what is best for you.

Want to print this list of tips? Download the printable version here. Interested in more details on this advice? It is all covered in detail in my online dating guide.


About the Author:

Brad initially struggled with online dating but over time became quite successful using it. He met his wife using online dating and has been giving advice and helping people improve their results since 2007. He has written a Free Online Dating Guide to help others find success with online dating. You can learn more about his personal experience using online dating and running this website here.


  1. Pamela  November 17, 2012

    I have done online dating off and on for 5 years. I used to have a phone call after 2 -3 emails and than a meeting after the phone call.

    Recently,,,the last 3 men I have talked with…I wasnt quite sure how i felt, something in my gut was telling me to go slow. I spent a long time with email (thankfully)

    The first withheld important medical information and when i didnt hear from him for a few days i wondered…then he told me he had a heart attack and was hospitalized.

    The second one let it slip that he had been institutionalized and had mental health issues….and some other concerns…as we talked about the election and at my opinion he used fowl lanuage to curse at me..

    The one I met this week on POF…I told in the first email that I didnt feel we were a match…I just went back and read my sent messages, and i have told him that every day yet he persists that we are. He said i was hateful, stern,mean, when i told him i have no interest. Then he threatened me to contact the site and say that i threatened to harm him….so 2 days ago i told him i was sick so i have tapered off returning emails. If he does not stop I will cancel my profile.

    So you see, there is some benefit to waiting. However, this was POF. On match, i have met really great people who have no problem telling me where they work, putting my mind at ease..And maybe this was a fluke as I haven’t run into these problems in the past.

  2. Carl  April 18, 2013

    Great advice, really. Thanks Brad.


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