Avoid a Bad Date with The 5-Phase Online Dating Approach

I try to avoid bad dates (though sometimes, there’s simply no helping them), so I developed a 5-phase approach to online dating that helps ensure I don’t end up on the date from hell. During each phase, you have an opportunity to weed out the duds!

PHASE #1: Online Messaging

Obviously, the first step to online dating is messaging back and forth with your dating interest.


It’s important to keep this phase short. Any longer than a week and you’ve ended up with a pen pal.

Important Questions to Ask During This Phase:

  • What do you do for a living?
    First, this helps ensure they are actually employed. Second, well, this helps ensure they are actually freaking employed!
  • How long have you been single?
    Weed out the “about a month” profiles… they’re in rebound mode at this point. Good answers are 6+ months.
  • Where do you live?
    Confirm their location. I’ve met some dudes with profiles that say my city, but they are actually located elsewhere… “Yeah, I live in New York right now, but I’m headed back to CA soon.” No.

Red Flags During This Phase:

  • They immediately ask you out without asking you about yourself first.
  • They never ask you out (pen pal).
  • They get sexual right away – unless you’re looking for a hookup, this IS a red flag.
  • They only answer your questions, but never ask anything in return (their world either revolves around them or simply isn’t interested in sharing the universe with your world).
DATING ALERT: Speaking of red flags, check out these 20 Online Dating Message “Hello” Fails.

PHASE #2: Texting

The next phase is moving to texting with your dating interest. This phase gives you a sense of their schedule, texting style, and interest. Here are the Goldilocks and the Three Bears Texting Styles:

Porridge is Too Hot: Stalking

Some people will text stalk…

“Hey, how are you today?”
“Did you get my last text?”
“Thinking about you.”
“You having a good day?”

…and not once do you get a chance to reply.

Porridge is Too Cold: Sporadic or Delayed

Others will take forever to respond. We all have our phones with us at all times these days… why is it taking you 12 hours to reply??

Porridge is Just Right: Somewhere in the Middle

The best are those who text here and there each day to keep communication open, show their interest, and escalate communication to a phone call.

DATING TIP: Don’t try to get to know someone by text. A phone call is more appropriate for finding out who a person is. Texting should be used for showing interest, scheduling phone calls and dates, and staying in LIGHT communication to keep the ball rolling.


Keep this phase short. At this point, texting should mainly be a means to an end to setting up a phone call within 2-3 days.

Important Questions to Ask During This Phase:

  • When are you free to do a phone call?
    I try to NEVER go out with a guy I haven’t talked to on the phone first.
  • Can you send me a recent pic?
    Request a recent photo that is NOT posted on their profile.

Red Flags During This Phase:

  • They send unrequested photos.
    Some guys love to send me pics of them driving, reading a book in the law library, tasting vino at a winery, taking a selfie in the mirror… all without provocation. Can you say EGO?
  • They text you relentlessly.
    The eager beavers are a little too desperate and not so much interested in you, but rather in not being single anymore.
  • They take days to reply.
    They’re either too busy to date, workaholics, married, or just not that into you.
DATING DANGER: Are you sick of the dating texting mind games? So am I. Check out this post and vent with me: #IHateDating: Playing the Dating Texting Mind Game

PHASE #3: The Phone Call

This is the most important phase prior to a first date. It allows you to:

  1. Hear their voice (this helps you weed out guys that sound like girls and girls that sound like guys).
  2. Get an idea of their sense of humor (this is your chance to banter and see how well your humor aligns).
  3. See if you two can actually carry a conversation.
  4. Find out how intelligent they are… VERY important.
  5. See if there’s chemistry… yes, you can have chemistry over the phone.


The first call should happen within a few days of moving offline with your communication.

Important Questions to Ask During This Phase:

  • Now’s the time to ask more about the person. Who are they? Who were they yesterday? Who do they plan to be tomorrow?
  • Ask about hobbies and extra curricular activities.
  • If you’re digging the interaction, ask when they’re free for a first date.

Red Flags During This Phase:

  • After only a few minutes, either you or they want to end the call… no explanation needed on this red flag.
  • It feels awkward. If it feels awkward on the phone, it probably won’t get much better in person.
  • They don’t ask you anything about yourself… hello?!
  • You don’t care to ask them anything… save yourself the boredom and move on.

PHASE #4: Skype (optional)

One of the biggest complaints from online daters is winding up on a date with someone who doesn’t look the way their profile indicated they look. Video chatting is an easy way to avoid this awkward and disappointing fate.

This is an optional phase, as not everyone is comfortable or familiar with video chatting. You can always request recent photos (recommended in PHASE #2: Texting), but if you have the option of doing a video chat, take advantage of it!


You can merge this phase with PHASE #3: A Phone Call and this can be the pre-date date!

Important Questions to Ask During This Phase:

You should have already asked everything you need to know before the first date by this phase, UNLESS you have not had a call yet (in which case, reference PHASE #3 above).

Take this opportunity to enjoy flirting. However, if you’re at a loss for conversation, here are some appropriate questions for video chatting:

  • Why don’t you look like your pics?
  • Is that your wife behind you?
  • Is it cool if I just stare at myself during this chat?

Red Flags During This Phase:

  • You’re pretty sure that is NOT the same person you saw on the profile.
  • Their wife IS behind them on the screen.
  • Their home is a disaster.
  • They have “Hello Kitty” memorabilia on their wall.
  • They tell you to take your clothes off.
  • You DO take your clothes off.
  • They take THEIR clothes off.
  • You realize you’re naked Skyping with a complete stranger.

PHASE #5: The First Date

After following the above phases and embarking on the first date, you should ALREADY have a good idea of the following:

  • What they do for a living.
  • A little about what their humor is like.
  • They DO look like their photos.
  • You two can carry a conversation.
  • You have similar interests.
  • What their wife looks like.
  • What their favorite Hello Kitty poster looks like.
  • You have a genuine interest in getting to know them better.

Unfortunately, you won’t be able to tell exactly what the future holds for you two…

Thanks to my 5-phase approach to online dating, I rarely end up on a bad date. Hope it works for you too!

DATING TIP: Not interested after meeting in person? Here are 5 Ways to Say “No, Thanks” After a First Date.

Do you have any tips for avoiding a bad date? Leave your comments below!

Photo Credit: SplitShire

Internet's Top Dating Coach - Evan Marc Katz - offers dating and relationship advice to smart, strong, successful women... Click here to find out more!

Up Next

Avoid a Bad Date with The 5-Phase Online Dating Approach

Can You Date and Be a Smoker?

#IHateDating: The Time I Was Told I Was Too Big for a Relationship

20 "Hello" Online Dating Message Fails

VIDEO: The Who, What, When, Where, and Why of Our Past Loves


Author: Brookell

Welcome to SWD! This is my blog and my online dating hell.

Facebook | Twitter | Google+

Get the Latest, Every Friday

No shirtless selfies included, I promise.

Leave a Comment!