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How to Start a Conversation With An Online Date

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Tips for Online Dating Conversations

The conversations on online dating apps and sites are half the fun but not everyone sees it that way. For many, just figuring out an opening line is already nerve wracking.

Even though most of our daily conversations go through text and emails these days, some still struggle with messaging on the dating sites and apps. Where does all this pressure come from?

The truth is that messaging online should feel as casual as regular texting with one of your friends. There is truly no need to stress over every single word and spelling mistake.

Don’t believe us? Here are our top tips for online dating conversations so you can try for yourself.

Tip 1: Open with a Reference Question

One of the most common questions people ask about online dating is what should be their opening line. This is our answer: start with a question about something that you noticed on their profile.

Here are a few examples:

  • I saw the beautiful photo of you by a lake. I love swimming in lakes. Which lake is that?
  • Cute dog! What is her/his name?
  • I see you like to work out. Which would you choose: crossfit in the gym or jogging through nature?
  • Ok taco lover, your top 3 taco places. Go!

These questions show that you actually paid attention to their profile and are at the same time showing interest in their interests. There is much more for them to go on than just a simple ‘hey’. You also avoid the big mistake of seeming like the person that sends every match the same opening line.


Tip 2: Don’t Dwell on the Standard Questions

There is a reason why dating sites encourage you to create detailed profiles. It is so you can avoid the boring standard questions of where you work, where you grew up etc.

Sure, these are normal things to want to know about someone but how much does it really tell you about their personality? Think about it this way, how do you feel about having to reply to the 12th person asking you how your day has been?

The more unique questions make a person more memorable and that is what you want on a dating app. Be more than just a swipe right.


Tip 3: No Pet Names

How can you give someone you never met before a pet name? To most people, especially to women, it feels a little slimey.

So avoid the ‘hey handsome’ or ‘how are you, beautiful?’ and anything else along the same lines. They are not appropriate for online dating – save it for when you are actually dating.


Tip 4: Never Ever Say/Send Anything Sexual

With the exception of dating sites that are explicitly for hookups, online conversations are not the place for your overly sexual messages. It is simply off-putting.

This mostly goes out to the men; don’t do it! It is harassing behaviour and will get you blocked and reported within seconds.

The sexy late night messages are for much later in the relationship. For when you have already signed off from the dating apps and clearly expressed mutual interest for a sexual connection.


Tip 5: Questions Go Back and Forth

When they ask you a question, it is only logical to ask them the same question back. Often, their questions are their way of steering the conversation to something that they enjoy talking about, too.

The conversation quickly becomes one-sided when only one person is asking all the questions. It shows that the person who is doing all the answering is not really interested in the person doing all the asking.

Recognize this pattern in your conversations? It is a sign to move on to the next match.


Tip 6: Change the Subject to Keep the Conversation Going

After the first few questions and replies, you might have run out of things to say about that particular subject. The best thing to do at this stage is to steer the conversation to another subject.

This prevents the conversation from feeling forced and gives you the chance to learn more about the other person. Don’t worry too much about a smooth transition, either.

If you are switching to a completely different topic, make light of it. For example;

  • (enter smooth transition) what is your favorite thing to do on a Sunday?
  • Before I start to bore you, let me ask you something else.

Tip 7: Don’t be Closed Off

If someone asks you genuine questions, give them genuine answers and not just one liners. The point of online dating is that you get to know other people which doesn’t work if you have nothing to say.

There is no need to write an entire sonnet for every question they ask you. Just remember to throw in 2 – 3 sentences every once in a while and elaborate when they give you the space for it.

Tip 8: This Is Not a Therapy Session

A common mistake that online daters make is putting it all in the online conversations and leaving nothing for the actual date. The messaging is just the interlude to a date so there is no reason to turn it into a therapy session.

Online conversations should be kept light and breezy, as a feeler if you could enjoy a cup of coffee together. If the conversation is pleasant and you would like to get to know them better, suggest a date. That is when you can ask the bigger and deeper questions.


Tip 9: Don’t Let It Drag On

Another common mistake in messaging on dating sites is that people leave it at the online conversation. Again, the point of online dating is getting to know new people and for that you need to go on a real life in person date.

So, instead of letting the online conversation drag on for longer than it needs to, go ahead and suggest a date. You don’t have to immediately commit to 3-course meal or 2-hour hike – just coffee is the perfect first date.

The problem with letting an online conversation go on for too long is that you create time to lose interest. There is only so much that you can learn about a person through text. You won’t know if there is a true click until you have met them in person.


Tip 10: Mind Your Spelling

As it turns out, bad grammar and spelling are a major turn off in online dating. Nobody is expecting you to type 100% correct English but consistently poor sentences and misspelled words are doing you no favors (with the exception of people whose first language isn’t English).

Apparently, typing ‘u’ instead of ‘you’ and ‘rly’ instead of ‘really’ makes you seem lazy and uncommitted to the conversation. Practice typing out the complete word and use regular sentences with your next conversations if you want to leave a good impression.

These 10 tips already make a big improvement on your online dating conversations. They may seem simple and logical but many people forget about them. If it helps, keep this article open in one of your tabs as a cheat sheet for your next online conversation.

Online Dating Tips for Older Women

Reading Time: 4 minutes

Online Dating Tips for Older Women

Online dating as an older woman is great! Don’t let anyone tell you that datings sites and apps are only for the twenty-somethings.

There are more single men over 40 on dating sites than there are women. This means that you have the upper hand and get to take your pick.

You would be surprised at how desired older women are on dating sites. If you let yourself, dating as an older woman can be a whole lot of fun.

Need a little nudge to get in on the action? These are out online dating tips for older women.


  1. Accept that Experience is Sexy

Don’t compare yourself to that twenty-something fresh graduate that is just now starting her adult life. There is no comparison, you are not in competition.

The only thing your age means is that you have more experience and men find this very attractive. The younger men would love to learn from you and the older men are relieved to meet a woman that knows what she wants.

Whether you decide to go younger or stick to someone similar in age, your experience is a magnet. Take all the best things you have learned over the years and leave behind everything that is not worth your time.


  1. Date Younger Men

Of course, there is some truth in the stereotype of men dating a younger woman during their midlife crisis. Again, this has nothing to do with you.

These men are looking for excitement and you can find it, too. There are plenty of younger men on dating sites looking for an older woman.

It is not for everyone but dating someone younger can feel very good. It is a great kickstart to your new dating life, especially if you have been off the market for a while.


  1. Sign Up for the Bigger Dating Sites

There is a niche dating site for every type of fancy but we don’t recommend these for older women. Online dating still remains a numbers game so the more popular sites are your best bet.

Match, EHarmony and Elite Singles are the 3 biggest dating sites if you are looking for serious relationships. You can opt for Christian Mingle or JDate if you prefer faith-based dating.

It might be better to stay off the regular dating apps because their crowd tends to be very young. Unless, you are interested in lots of one-time dates with twenty-year-olds. There are also certain dating apps that cater to more of a monetary relationship. One such app is called Seeking Arrangement (you can read a full Seeking Arrangement Review here), which provides sugar dating connections to people all over the world.

  1. Take Amazing Photos

This next tip is to give yourself a confidence boost. At the same time, it shows whoever views your profile that you feel good in your own skin.

You don’t have to get professional photos done to have great photos. On the other hand, if you have the time and money for it, why not?

Whether you spend an afternoon taking photos with a friend or pay someone to do it, get it done. Fantastic photos are the first thing people notice on your dating profile, your age comes later.

  1. Send the First Message

Again, confidence is one of your greatest assets as an older woman. Show your confidence right from the start and send the first message.

Have a few lines ready for each time you match with someone. Don’t be afraid to start the conversation – men really do appreciate it.

Want to start with something cheeky? Ask them who their favorite actress over 50 is: Sandra Bullock, Halle Berry, Demi Moore?


  1. Ask Them Out for a Drink

This tip applies to everyone that is online dating; don’t keep messaging for too long. Too many people are too comfortable messaging back and forth without every setting up a date.

The instant messaging is a great filter system but that is not the goal. The goal is go out and physically meet new people to find out if there could be a spark.

So, give yourself a maximum of 3 days of messaging and then ask them out for a drink. Yes ladies, you should be the one to ask them out.

  1. Be a Little Picky

You often read that dating experts advise you not to be too hung up on your selection criteria. The idea behind this is so you don’t miss out on great guys over superficial characteristics.

There is some truth to this but it deserves a nuance for when older women dating online. At this stage in your life, you have probably already met quite a few men that you wish you didn’t.

Our advice is that you do let go of the superficial criteria but definitely keep high standards for the most important things: personality and values. Trust your gut on whether your personalities match or not and wait for someone that has the same values as you.



Bonus Tip:

Is online dating not for you? Or have you been on the dating sites for so long that you are tired of swiping?

It is perfectly okay to take a break from the online dating scene. After all, it is not the only way you can meet someone.

If you are feeling a little gutsy, you can try to reconnect with someone from your past. Perhaps an old flame or that guy that you never had the courage to ask out before.

Giving it a go with someone that you already know can feel a little more comfortable than online dating. You never know how different things could be after all this time.

Your age is not something to feel embarrassed about. it is something you should embrace and wear it with confidence.

Feeling good about yourself makes a huge dating when you are dating. Start there before you start swiping.