How to Successfully &  Safely Flirt Online (Part 2)

Posted On: September 22, 2014 0 Comments

In my last post I talked about how to successfully flirt online. The focus was on keeping it light, funny and to test the waters to see if the two of you should actually go on a real live date.  While flirting is fun, it can leave you vulnerable to some online dangers.

Just because they may be far away on the other end of a computer, cell phone  or video camera, it’s still important that you keep your safety in mind when flirting virtually. I’ve included some of my best tips for staying safe while dipping your toe into the dating pool to flirt online.

Online tools are your first line of defence

Before you do anything, prepare new online accounts

Flirting online tipsThe very first thing you should do before you flirt online (or set up an online dating profile) is to set up an email and online chat account (Skype, Yahoo, Google) that does not include: your real name, picture, phone number, address, home location or connection to your work. It’s best to keep your dating email and exchanges on a separate email account so you can keep them safely quarantined from the rest of your life.

I am not suggesting that you lie or put up a fake catfish style profile. But, it is important to keep that information under wraps until you get to know someone better and feel confident you can trust them.  Once you let that wall of protection down and information out you can’t take it back.

Keep communicating though the dating site as long as possible

While it may be tempting to give them your personal email address or other access to you outside of the dating program, it’s best to go through those structured sites until you really get to know someone better.  Those sites are your first line of defense in staying safe online.  Once you give out your direct email, video/ chat account or cell phone number it becomes that much harder for you to keep a safe distance.

Don’t give away your coordinates

When you’re flirting and chatting don’t give out personal details that will make it easy for them to locate you. Don’t disclose where you live or work, keep that information general. Also, you don’t want them showing up at your home or work unexpectedly (which by the way is very high on the creepy scale). Remember right now it’s just about getting to know the person in a broad sense. Flirting is meant to help you determine if there is enough spark to warrant a real date.

Don’t broadcast your social media

Don’t  share your social media accounts if you can help it. I know this becomes harder if you meet through something like Facebook or Twitter. At least don’t make it too easy and remember that you do have the choice to connect with them or not if they make the request. Check out my previous article on keeping your social media private for tips on how to do that and why it’s important.

Trust Your Gut

  • Don’t feel pressured to over share
    As you’re flirting and getting to know someone online don’t let them pressure you.  If they push you for identifying details, want more direct access to your online life or keep asking you to take the conversation off the dating site or offline, take the opportunity to set some boundaries.I recommend that you tell them directly that you prefer to keep that information protected while you’re getting to know anyone new online.  Someone worth getting to know will understand the logic of that and won’t push the issue.  It’s actually a helpful litmus test to see if the person you’re talking to is respectful of boundaries and is truly interested in getting to know you for the right reasons. If they do push for more information then you want to share, take as a sign that it’s probably time to move on.
  • Love at first click
    Online , dating, online dating, relationashipsIf you flirt with someone online and they start to tell you how beautiful/handsome you are, how much they love you and maybe even that they’re ready for some deeper commitment like marriage, beware!  Actually don’t just beware, run! They are one of two things: (1) Unstable and needy or (2) They are trying to scam you one way or another.  While attraction can happen quickly and the attention certainly feels good, it’s important to keep your head about you while you flirt.  Don’t get taken in by an emotional or financial vampire. Love takes time and flirting should be taken slowly. Anyone approaching it at lightning speed has another agenda going on and one you want to stay away from.
  • No one has the right to make you feel uncomfortable
    If someone you’re flirting with online makes you feel uncomfortable, you have every right to stop communication with them. No one has the right to creep you out and you certainly don’t have to keep taking it. If they say inappropriate things, push you for intimate information or make off color remarks, you can and should end communication. You can either tell them why you’re ending it or just end it.  The more disrespectful and creepy they are the less necessary it is that you provide a reason why you’re done talking to them.
  • It’s just doesn’t feel right
    Trust your gut and if after flirting with someone for a while it’s just not feeling right, you’re not obligated to keep doing it. If it’s just a matter of no sparks, just let them know it was nice chatting but you’re just not feeling a romantic connection.  If they are being creepy see the paragraph above.

How to flirt onlineI know that much of this seems repetitious. But when we live so much of lives online it becomes harder to know how to be safe about the information we share. Often we take online communication for granted, have a false sense of security and never realize we’re potentially putting ourselves in danger.  The bottom line is that we do have a choice about what information we share and how we share it.

Hopefully this didn’t suck the fun out of online flirting for you.  With just a few precautions online flirting can be a great tool to help you weed out the good prospects from the bad and get you that much closer to successful dates and lasting relationships. Flirting can make or break a blossoming relationship so make sure you know how to do it safely.

Cija Black WInk Wisely Guest Post

Cija Black is a love expert, author, blogger, online educator and host of the “Love Bombs” podcast. For more information about Cija, the books, class or podcast, visit

Posted On: September 22, 2014 0 Comments

How to Successfully & Safely Flirt Online (Part 1)

Posted On: September 18, 2014 0 Comments

Since the dawn of time there has been flirting in one form or another.  From coy glances through the tribal fire, over a lace fan or across a crowded bar, flirting has always been part of the process of falling in love. It’s how we show interest in someone and also see if they’re interested in us.  Some of us are more successful at it than others.

Your  eyes say yes, but your lips say no

How to flirt onlineBefore the internet, the main way to flirt was face-to-face. It was done through looks, eye contact, body language and tone of voice. Technology has added a whole other set of tools to the flirting arsenal. Now you can flirt through online chats, with texts, emails, Facebook pokes and all manner of online communication. Some dating sites even have their own special apps specifically designed for the flirting portion of getting to know someone.

How you use flirting can either help or hurt your quest for love. But the question is,  are you really using it to your advantage and are you flirting online safely? No matter where your flirting takes place, you still to know what to say and how to say it.  Below are things you should be including (or not) in your online flirting attempts.

First impressions are important

If you’re online, odds are you’ve gotten some unsolicited flirting emails or comments directed your way from fishers, scammers and maybe even some legit admirers . Some may have a bit of class, but most are usually kind of gross. That is not how to flirt online, it’s the equivalent of saying, Hey baby, come here often?” to someone in a bar. It’s tacky and ineffective; at least it is with the people you’d want to date.  There are much better ways to flirt online.

  • Have a sense of humor
    If you have a sense of humor share it, if you don’t develop it.  Laughter (even the LOL kind) and joking around is a great way to break the ice, find common ground and get a conversation going.  It’s important to note that not everyone has the same sense of humor and jokes made at another’s expense are in poor taste.  Find common ground, gauge your audience and share some laughs.
  • Don’t be creepy
    While creepy can be in the eye of the beholder, it’s generally anything that makes someone else uncomfortable.  Holding a look for too long (on video chat), saying things that are intrusive, inappropriate or overtly sexual are all pretty creepy. One way to tell if you are being creepy is if the conversation is flowing and then suddenly comes to a crashing halt, they get silent or end the conversation and maybe even vanish .  Dial it back, respect boundaries and if the conversation doesn’t get back on track it’s probably best to end it.  Creepy is never sexy and I would be wary of anyone that’s taken in by it.  They most likely have some issue of their own.
  • Don’t be misunderstood
    One of the greatest challenges of flirting online is that there is so much that can be misunderstood.  You don’t have the benefit of body language and tone of voice when connecting with someone online. It’s easy for people to misread your intentions, attempts at humor and what you’re looking for.  For this reason,  keep the flirting light, simple and to a minimum at least until you meet in person.  If they ask you what you mean or for some sort of clarification in what you’ve said, be honest and tactfully direct. Head off any misunderstandings early so that you don’t get off track.
  • Get to know your audience and respect their boundaries
    Just because you’re online and may not be able to see the other person, doesn’t mean you’re free to say anything and everything that comes into your head. When flirting don’t dive right into super personal things or into being too sexual.  It’s creepy and predatory.If someone asks you to change the subject, be willing to respect that request and stop. If you don’t, you’ll most likely blow your chance with them.  Boundaries are not in place to see how far you can push them, they are there to let you know what the other person is comfortable with. Respecting boundaries will go far in helping you to know someone better.
  • Don’t bombard them with endless emails or texts
    If you are interested in someone you meet online,  send them one email and wait.  Not 10 everyday for a week.  Give them a chance to decide if they want to respond. Sending a relentless barrage of emails is like pushing the elevator button repeatedly. It’s not going to get there any faster the more times you push.Remember, that at the other end of the email you’ve sent is a person with a whole other life. That life includes things like work, home life and other potential matches.  Just because you like them, doesn’t mean they feel the same way about you. Pushing for a response isn’t going to convince them to see things your way.  Most likely that kind of persistence is going to earn you the label of creepy and odds are you’ll end up deleted and blocked.
  • Be honest
    dating, online dating, matecheckWhile flirting is just the beginning stage of getting to know someone it’s no reason to start off with lies.  Don’t say things you don’t mean or just because you think that’s what they want to hear. Don’t lie about who you are, your age, your weight or financial status.  While it’s not necessary to disclose all of this in the flirting phase of things, there is also no reason to lie if you are asked about it. Kick it off with honesty. If they have issues with who you really are from the beginning ,there is no reason to pursue flirting with them any further.
  • Flirting is a tryout for a first date keep it fun
    Keep the communication light and don’t get too heavy too fast.  Don’t declare your undying love for them as an opener to the conversation or blurt out that you are slogging through a rough breakup and need a shoulder to cry on.  Flirting is your testing ground to see if a real live date is in order. Keep the conversation fun, flirty, light and engaging and save the heavy baggage for a more appropriate time.  NOTE: If you feel compelled to get heavy too fast you may need to step back and take some time to get your baggage squared away first before flirting and certainly before any serious dating.

Online flirting is a lot like in person flirting.  It’s about keeping it fun and light and is really the tryout for a real live date.  The other side of this is keeping yourself safe while flirting online.  Stay tuned for Part 2 of How to Successfully &  Safely Flirt Online.

Cija Black WInk Wisely Guest Post

Cija Black is a love expert, author, blogger, online educator and host of the “Love Bombs” podcast. For more information about Cija, the books, class or podcast, visit

Posted On: September 18, 2014 0 Comments

When Online Dating Turns into an Investment Opportunity: Say Goodbye

Posted On: September 12, 2014 0 Comments

"I think UR a Cutie... Do U wanna make $$$?" Do not fall for it.

Hamilton RCMP are searching for a 50-year-old Toronto man they say targeted victims through online dating and then solicited investments into his company.

Glenn Whitter, 50, is wanted on a charge of fraud over $5,000.

One victim who came forward to police said she was targeted through social media and then asked to invest in Cretus Capital Incorporated, police said.

Via The Hamilton Spectator (Read More)

Need an example for why you should not give money to people you meet through dating sites? Hamilton RCMP is currently running a manhunt for a 50-year-old suspect accused of defrauding women online. This case goes to show that it is possible for anyone to run an online dating scam, so it is crucial for everyone to understand the warning signs.

  • Does that profile picture look too good to be true? People who commit fraud online will often use pictures taken from other profiles, or even use found images from the web. You may be able to spot a stolen profile with a reverse image search, especially if there are older copies of the picture that belong to other people. If they are using their dating, online dating, matecheckown pictures, it’s still not a guarantee.
  • Are they asking you for money? Never give money to someone you have only met on the internet, even if they say it is an emergency and you are the only person they can contact. The Spanish Prisoner letter is as old as postage itself. If it was really an emergency, an online dating site would not be the appropriate place to find help. Do not ask them to explain themselves; they will take this as an opportunity to convince you. Instead it is best to block, report, and move on.
  • Are they offering an investment opportunity? Ask yourself: “Why am I getting an investment pitch through an online dating site?” If you have not met the person involved, if you have never heard of the business before, and especially if you are having the discussion through an online dating site’s chat service, say goodbye. Whoever is writing the investment pitch is interested in manipulating you, not dating you.
  • Are they offering to give you money? This is a red flag for a money laundering scam. If you accept and transfer large sums of money for someone you meet online and it turns out they are laundering money for a criminal organization, you may wind up facing criminal charges yourself. This June, a man in the UK was taken to court for being duped into becoming a money mule for a terrorist organization.

There are online tools that can help. MateCheck provides a self-verification service that includes identity verification (name and age), criminal background checks, bankruptcy verification, and verification over whether a divorce has been filled. No matter what you choose to do, stay safe, and do not transfer money or any private account information to online dates.

Posted On: September 12, 2014 0 Comments

Baggage Claim: Owning Up to Your Past and Learning to Share It

Posted On: September 8, 2014 0 Comments

I recently had some trouble deciding whether or not I wanted to be in my relationship. This is nothing new for me, I have a history of sabotaging my would-be relationships because I get scared of commitment – or maybe I’m scared of love…I’ve never quite decided. All I know is that this time I instantly regretted my reaction to flee and I met with my sister (who is, conveniently, also a therapist) to discuss my latest love-related mistake.

Sharing personal baggage is always difficult.My sister, being both a therapist and soon-to-be newlywed, provided me with some very enlightening (albeit somewhat harsh) information. She sat me down over gelato and told me that I have a lot of baggage…as if this was news to me. But she didn’t mean it as an insult and what she said got me thinking. It’s no mystery to me that I have enough baggage for a year-long trip around the world or that I have commitment issues matched only in grandeur by George Clooney, but that it’s the combination of the two that makes for a deadly combination. I have a lot of fears, a lot of past dating-horrors, and yet I speak of none of them.

If only there were a way of displaying all my baggage to the person I’m dating before we get too far into the relationship…

When Going On a Trip, Would You Leave Your Baggage Behind?

Dating is a journey. This trope, though an overused cliché, is no less true. Both parties involved begin at an introductory stage and continue down the road together through phases of experimentation, intensification, integration, and bonding, then – if you’re among the lucky ones – you will continue to bond and never see the stages leading to termination. But like every journey, no matter the length, you always need to bring along some baggage. So, in the words of the great Bill Nye: “Consider the Following!”

A short journey (ie: to the store, the gym, to work) requires one to bring along his or her small baggage such as a wallet, gym bag, work clothes or shoes, et cetera, while a slightly longer journey (ie: weekend trip, out of the city trips, etc.) require slightly more in the way of luggage – perhaps a weekend bag or at least enough clothing to last a few days, a toothbrush, toiletries, and so on. Long trips, on the other hand (ie: out of the country, a permanent move, etc.), insist that one brings all of his or her effects along. Furniture, clothes, books…everything must go (as they say)! Intimate journeys based in romance may be looked at much the same as the physical trips of everyday or vacation.

It’s always best to be prepared and bring as much as you can to get the job done but the longer the voyage, the more baggage needs to be brought. You cannot expect to live out a long-term relationship to its fullest by only bringing along a limited amount of your baggage. It is important to bring it all with you and use it to further your relationship with your partner. Use the sharing process as an instrument of trust rather than hiding behind it out of fear.

But What of the Baggage Blockage?

For people like me, the temptation to abandon ship mid-trip is an overwhelming prospect and my sister knew this from my past experiences. While speaking with her, I happened to mention, “if only there was some kind of place for people beginning relationships could be honest about their feelings, their desires, and display all their baggage at one time”. She looked at me and laughed. “There kind of is, sis,” she said, “it’s called online dating”.

Online , dating, online dating, relationashipsHaving forgotten that she met her fiancé online, I felt like an oblivious fool. Traditional, in-person dating encounters often present the daunting task of verbally sharing past treasures and trespasses while requiring a certain level of trust on behalf of the other person. One of the perks of online dating is being able to lay out all your baggage, prior to any heavy commitment. My sister and her fiancé are a walking testament to the wonders of the online method as, not only does it make baggage claim easier, but they have more trust in each other than I have seen between many people in my life. Granted, online dating site users must still beware of catfish and other cyber-sneaks, having your much of your background posted on your certified profile certainly helps to open the lines of communication in a positive way.

Sharing your baggage is always difficult. It requires a certain level of openness, tact, and – above all else – vulnerability. And while online dating is just as terrifying as meeting the “old-fashioned way”, the dating game will always boil down to the simple fact that baggage claim is a necessary evil. If you want to love and be loved, you need to declare everything. Once you cross this border, your journey may finally become the adventure you always dreamed it would be.

I know mine is.

Dana Simpson - author for WinkWisely.comDana Simpson is a writer, musician, and university graduate.  Not surprisingly, literature and music are her greatest passions in life alongside travel, human rights and art as a means to social change. Follow Dana on Twitter (@danasimpson) and read more of her work at

Posted On: September 8, 2014 0 Comments