The ongoing feud between Kendall Jenner and Taylor Swift has emerged recently in the press. Apparently the singer still feels betrayed by her one-time friend, and Kendall isn’t acknowledging she did anything wrong by dating Swift’s ex-boyfriend Harry Styles.

“Harry’s always been the biggest issue between them,” according to a report by OK! Magazine. “Taylor thinks it was completely disrespectful for Kendall to be hooking up with Harry after he broke Taylor’s heart.”

Dating a friend’s ex has always been a thorny subject. Does your loyalty to your friend mean that you never cross that particular boundary, even long after they have split? Or should you cast aside your grievances with your ex so that it’s not an issue if your friend ends up dating him?

When two people have split, they are free to make their own decisions, including who they decide to date. Some people are more reluctant to risk friendships than others. Some are more motivated by their passion, so they end up choosing risk because the feeling of love will outweigh the bonds of friendship.

If you are considering dating your friend’s ex, there are several things to consider first – because remember, once you start down that road, you can’t really turn back:

How strong is your friendship? Have you known each other for years, seen each other through break-ups and hard times, or are you relatively recent buddies, or hang out with the same group of friends on the weekend? The level of friendship matters – you’ll feel more loyalty towards someone you have known a while, so you might not want to risk the friendship. On the other hand, if she’s more of an acquaintance, you might not feel bad letting the friendship go.

Are you motivated only by passion or chemistry, or something deeper? Is this just a flirtatious chemistry between the two of you, or are you just curious to see what he’d be like? If so, you might want to reconsider dating your friend’s ex. Think about the pain you might cause her just because you want to act on your impulses. There are plenty of other guys out there.

Have you discussed your feelings with your friend? Maybe you are drawing conclusions that are false. Maybe she wouldn’t mind you dating her ex, or maybe she would and you are giving her the opportunity to vent. Admitting your feelings to your friend is an act of courage and respect for the friendship – don’t hide and sneak around until she finds out. Own your feelings, and be open about what you want.

Are you willing to let go of the friendship? This is the tough question, because we want to have our friendships and love. But if your friend is hurt by your actions, you must allow her that space to grieve so she can heal. That means not demanding her friendship or understanding. Let her process her pain. Maybe she will want the friendship in the end, or maybe she won’t – ultimately, when you make that type of choice, it’s up to her to decide what to do.

It happens in dating – you meet someone, you exchange numbers or friend him/her on Facebook, and then you want to reach out. Maybe you can’t stop thinking about him, or maybe he left a good impression when you first spoke. Regardless, let’s say you’ve had a few drinks and you’re feeling pretty fearless.

Next thing you know, you’ve sent a flirtatious text to someone you don’t even know that well. Maybe you are feeling more fearless when a couple of minutes goes by with no response, so you send another, flirtier message.

Soon, you’ve sent five messages with no response, and now you are sending yourself into a tailspin of negative self-talk. What is wrong with me? You ask. Why isn’t he texting me back?

At some point, likely the next day when you are picking up your phone to go through your emails, you look back on those texts you sent and cringe. Then the negative self-talk increases. Why did I have to text him so many times? What is wrong with me? Why did I text him at all?

We all do things we regret. Not every social encounter where you feel attracted to someone is going to result in a date. And there is a lot of pressure involved in reaching out to someone you don’t know – what do you say? Will they get your sense of humor? These anxieties we harbor make it much easier to communicate when we are not “in our right minds” – so to speak. Maybe you should have waited to reach out until the next day, or maybe you should only have sent one text instead of five. But what’s done is done, and it’s important to move past it.

Instead of feeling embarrassed and ashamed, it’s time to understand that communication slip-ups are part of the dating process. We all make mistakes. We misunderstand each other. You in all likelihood have received drunk or regrettable texts from other guys, too.

There is nothing wrong with making yourself vulnerable or expressing your interest in someone else. But when you obsess over a mistake, you are preventing yourself from moving on. Instead, you get wrapped up in your own patterns and behavior. But really, we should all take ourselves a little less seriously, and take respect and caring for others a little more seriously. In fact, extending compassion and kindness to your dates who just weren’t right for you – whether it’s because they drunk texted or you just aren’t into them – is the way to a better dating environment for all.

If you regret sending that text, make the decision to accept your mistake. And understand that just because you didn’t get the response you were after, it doesn’t mean you suck at dating and you just shouldn’t bother. In fact, it’s good to remind yourself in these moments of all the things you are – a good person, smart, kind, and respectful. Dwell on these positive self-talk messages for a while, and again, extend that kindness and forgiveness to others. There’s no need to be snarky in your own dating life.

On Sunday June 14^th, people across America were acknowledging Flag Day, an annual tradition, over social media. Coincidentally, it was also the annual celebration of the LGBTQ community – an event known as Pride. So when Coffee Meets Bagel reached out via social media to announce its support of Flag Day, the online dating service mistakenly caused an uproar because of a typo.

The now-infamous tweet which was widely criticized over social media and the subject of a story in the Washington Post, said: “It’s Fag Day. Hoist your colors and don’t forget to LIKE today’s Bagel.”

People on the East Coast were the first to catch the mistake, but many didn’t realize it was a typo and immediately took to Twitter to denounce the dating service, with one person posting: “Got a notification from @coffeeMbagel saying today was "fag day." I'm disgusted at the audacity to say that during pride. #coffeemeetsbagel.”

Many people weren’t aware of Flag Day, but they were aware of Pride celebrations, which made the typo even worse. They thought the company had posted the tweet on purpose.

Coffee Meets Bagel took down the post after they realized the typo. But thanks to the speed at which social media can influence a story, and the incredibly bad timing that the typo happened during Pride, the company had little chance to correct the error. They have since been apologizing and repeating that it was just a simple mistake.

About three hours after the notification went out, users received an e-mail from the company’s head of customer experience apologizing for the misspelling. It reads, in part:

“I would like to apologize wholeheartedly for the message you received this afternoon. The misspelling of Flag Day was a mistake and a complete oversight. We’re updating our process to ensure something like this does not happen again…Coffee Meets Bagel, as a company and as individual employees, celebrates the LGBTQ community and would never use such a word.”

While it might just be a simple oversight, the bigger question is: will it hurt CMB in the long-run, if people associate their brand with a lack of support of the LGBTQ community?

We have all sent emails and social media posts with typos – this isn’t uncommon. What is a shame in this instance is that a company sent an official tweet meant to show support of both Flag Day and the LGBTQ community, and yet, ended up alienating their customers and potential customers in the process.

Many of us have anxiety when it comes to first dates. After all, you’re expected to make a good impression in front of a total stranger. But what happens if you say the wrong thing, or there’s a pause in the conversation?  Or what if you’re not feeling so attractive or desirable? These things can affect the date itself, and how you feel about the person you’re meeting.

You don’t want to start off on the wrong foot. But it’s also important to approach it with a sense of humor and non-attachment, so that your anxiety doesn't take over.

Like with job interviews, sometimes first dates just take a little practice. They are a way to see if you have a connection – not if you can impress another person so much that they’ll fall instantly in love with you.

The mistake many of us make is that we think there should be instant chemistry on a first date, so it makes the pressure to create the chemistry even greater. But chemistry can take time to build, and often happens only when we show our vulnerabilities, when we decide to be honest in the moment and share our truth. That allows your date to open up more to you, too.

Following are some tips to help take the pressure off of first dates – and hopefully create an environment for connection:

Pick a location where you can feel comfortable. Instead of going for the latest trendy bar, or an expensive foodie experience, think of where you like to spend time. Is it at a museum, or low-key cafe, or at the brew house down the street? Pick a place that is enjoyable for you – it helps ease an already pressure-filled situation.

Pick an activity instead of a coffee date. Sometimes even the idea of sitting across from a stranger and trying to come up with witty conversation is just too daunting. Instead of putting yourself through that, take the pressure off by engaging in an activity. Go for a hike, or bike ride, or outdoor concert. Whatever you decide, it will provide you with something to talk about and ease the pressure to impress.

Invest some time – don’t date back to back. Some people life to be efficient and schedule dates back to back in blocks of "free" time. But this can create anxiety as well – and you never really enjoy each date because you’re looking at the clock. With a good date, you are totally in the moment. So don’t overschedule – or you set yourself up for failure.

Choose an outfit that makes you happy. Uncomfortable heels aren’t a requirement on a first date. If you love your Converse, dress them up with a flirty summer dress. Don’t be afraid to show off your style, and try to wear something you’ve worn before. If you feel good and comfortable in what you wear (and not constantly pulling up your bra straps, for instance), then you are more relaxed on the date.

IAC is no doubt a leader in the dating market, with such prominent online dating brands as Match.com, Tinder, and OkCupid, which make up a company subsidiary called The Match Group.

The Match Group has announced its plans to launch its first IPO, making the company available for investment dollars from the general public. Match.com has long been a cash cow in the online dating industry with its paid subscription service, and Tinder with its new premium paid service has been reported to be worth about $1 billion by the end of the year. In fact, the combined revenues of all the companies in The Match Group accounted for nearly one third of IAC's overall revenue in the most recent quarter. They're also growing rapidly, surging 13% year-over-year in the most recent quarter to about $239 million.

Greg Blatt, Chairman of The Match Group said in a statement: "The Match Group is poised for substantial growth in the coming years. The dating industry has come a long way since its inception, but the category remains underpenetrated.  We believe the combination of our more established businesses such as Match, Meetic, and OurTime, and earlier stage businesses such as Tinder and OkCupid, creates an attractive combination of significant cash flow generation, strong margins and meaningful growth potential.” 

This comes at a good time, as Zoosk recently pulled its plans to launch an IPO, leaving the dating space wide open for potential investors. Ashley Madison, a dating site for infidelity, was quick to throw its hat in the ring, too. They are planning a second attempt at an IPO for later this year after a forfeited attempt in 2011.

The Match Group joins other prominent and publicly traded online dating services, notably Spark Networks, which owns several niche dating sites such as JDate, Christian Mingle, and BlackSingles.com, as well as Jiayuan.com, the largest online dating site in China.

After the IPO, investors will be able to buy stock in the company, although the ticker symbol is not yet known. Notably, IAC made the decision to split The Match Group from its parent company to do the IPO.

Barry Diller, IAC’s Chairman and Senior Executive said in a statement: "As many know from our actions over the last 20 years, I'm not a believer in simply agglomerating assets in perpetuity.  I've long felt that as entities grow into size and maturity it's healthy to give them separation and independence from a mother church.”

After two years together, POF has ended its relationship with speed dating and singles event company FastLife.

POF CEO Marcus Frind saw a bright future for the union in 2013. "The direction of online dating is undeniably headed towards a merging of the online and offline worlds,” he said. “Currently our users host over 300 events worldwide each month. Now more than ever, we understand the importance of offering singles innovative, new ways of connecting face to face."

The plan was for POF to invest $30 million into live events over a period of 12 months. Competition in the arena was ramping up. Mega-companies like Match had introduced live events. Services like HowAboutWe were focused on getting online daters off their computers and into the real world. Location-based apps that linked nearby singles for insta-dates were becoming increasingly popular.

The time seemed right for POF to team up with FastLife, a company that held around 2,400 events a year in the USA, Canada, Australia, New Zealand and the UK. FastLife's exceptional service and venues generated annual revenue of ~$2.5 million. Could rounding out its offerings be what POF needed to take things to the next level?

The answer turned out to be 'no.' POF dropped FastLife in June 2015, 21 months after acquiring the company and 2 months after closing eVow. eVow had been launched to compete with dating sites focused on long-term relationships, but proved unsustainable after 5 years.

Now that POF has lightened its load, what's next for the dating site?

Like many of its competitors, POF is focused strongly on mobile. Frind told an interviewer at the 2015 Traction Conference in Vancouver that 90% of POF's business is now conducted on smartphones. POF is concentrating on keeping its brand strong, so mobile users will continue to choose it over other options in the app store.

POF is also concentrating on maximizing messaging. The more messages a user sends, the more likely they are to get a response. The more responses they get, the more likely they are to go on dates. The more dates they go on, the more likely they are to enter a relationship and have a successful online dating experience. Currently, around 30 million messages are sent each day on POF.

As far as revenue is concerned, POF has opted for a “freemium” model. Rather than a traditional subscription service, POF offers its basic features for free. Users can then choose to upgrade or add features for additional fees. With more than 100 million users and a rumoured $100+ million in annual revenue, it's hard to argue with the POF approach.