8 Tips for Online Dating Conversations

Are you looking for love? 2020 makes things a bit more complicated. Many people consider merely going to a bar risky, let alone meeting a stranger there. 

The answer, as in many COVID-19-created problems, lies in technology. You can meet a new love virtually — but you still need to think of what to say. Here are eight tips for online dating conversations to keep the discussion going and let you get to know the person “behind the mask.” 

1. Use Open-Ended Questions 

If you’re a parent, you know that asking your kids, “How was school today?” will result in a monosyllabic “fine.” Why would online dating conversations be any different? Besides, “How was your day” is a lame conversation starter.

Instead, arm yourself with tons of open-ended questions before you check your online dating inbox. You can find out a lot about your prospective mate. For example, if they reply, “a downtown Manhattan penthouse” to the “if you could live anywhere, where would it be and why?” question, you know to keep searching if you crave a quiet cottage in the country. 

2. Keep an Open Mind

If you use social media as a guide, you might think the world is polarized. While differences do exist, you must also guard against the propensity to stereotype others based on one answer. 

For example, if you dare broach the political conversation, you might ask, “What do you think is the most pressing issue of our time?” If you’re a treehugger, you might fall head over heels for someone who responds, “Passing a Green New Deal.” 

However, don’t shut out someone who replies, “expanding health care to all” or “ending racism and eliminating barriers to achievement for minorities.” Such individuals might also care deeply about the planet but have reasons to support other causes as well. 

3. Respond Sincerely 

You might think, “Who cares about little white lies online?” You will, if the chance to meet the right person arises and you have to explain the fib in person. 

Respond sincerely to the inquiries you receive. This openness makes the conversation more refreshing, and it also ups your chances of meeting someone compatible. 

This rule applies to your appearance, too. Let’s be real: No one wants to crash diet before a first date. It’s unsafe and can damage your health. Wouldn’t you rather have someone who accepts you as you are, a few extra pounds and all? 

4. Slow and Steady Wins the Race

Online dating isn’t a TV game show. There’s no need to rush from “Hi, how’s it going” to the first date in 30 minutes or less, minus commercial breaks. 

Feel free to trash messages along the lines of, “Hey, you look fine — wanna hook up?” Be safe and do you if that’s your wish, but if you want a relationship, slow and steady wins the race. Take the time to get to know each other’s personalities through messaging. It might seem old-fashioned or quaint, but it can lead to a stronger bond. 

5. Ask for Their Advice

Nearly everybody wants to feel like their opinions have merit. You can use this technique as a sneaky way to ferret out more information about a prospective partner while flattering them a bit. 

Let’s say you had some negative experiences, and you want to weed out anyone with narcissistic tendencies. You might keep the online dating conversation going by asking how they would react if a colleague took credit for one of their ideas. 

Run the other way if a prospective mate says they would find a way to get revenge or sabotage the other individual. Give the green light to those who say they would talk to the offender later or call a private meeting with their supervisor. 

6. Seek Shared Experiences

Imagine you spill your coffee on your blouse before a vital job interview. Then visualize the hiring manager putting you at ease by confessing a similar episode happened to them. 

You can create bonds over shared experiences — even embarrassing ones. If your would-be beau confesses to a time they got lost in the woods, share your story of embarrassingly getting turned around on a hike close to home. 

7. Talk to Multiple People 

Treat online dating conversations the same way you do job interviews. Don’t expect every connection to pan out — but do use these discussions as opportunities to get better at chatting with others virtually. 

No rule says you have to go out with everyone you talk to. Remember the old saying about having to kiss a lot of frogs before finding your prince (or princess)? 

8. Request More Information

Don’t be shy about asking for more information — once you establish trust. Understandably, you might feel nervous about giving out your digits if you had problems in the past with lovers who wouldn’t let go. 

Typically, people exchange numbers before the first date to make it less cumbersome to coordinate meetings. You can always use a free digital phone number such as Google Voice to keep your cell number sacrosanct. 

Safety Tips for Online Dating

You should protect your safety when preparing to get together with someone you met online IRL (in real life). Here are three tips to follow: 

  • Talk on the phone before meeting: You can’t always tell a person’s tone through digital communication. A voice conversation gives you more insight into their personality through their mannerisms. 
  • Meet in a neutral location: Netflix isn’t the best choice for a first date. Select a public place like a coffee shop with ample outdoor seating. Make sure you feel comfortable before heading to a more private location, which could take several dates. 
  • Have the mask conversation: You meet, the sparks fly — next comes the kiss goodnight, right? Yeah, 2020 threw a bit of a plot twist into that storyline. Have the conversation about wearing masks and taking other COVID-19 precautions beforehand, so you don’t feel awkward at crunch time. 

Use These 8 Tips for Better Online Dating Conversations 

Having better online dating conversations need not be challenging. The eight tips above will help you keep the discussion going and could lead to a meaningful relationship.