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How to ask a stranger out online

This article was co-authored by Maya Diamond, MA and by wikiHow staff writer, Hannah Madden. Maya Diamond is a Dating and Relationship Coach in Berkeley, CA. She has 13 years of experience helping singles stuck in frustrating dating patterns find internal security, heal their past, and create healthy, loving, and lasting partnerships. She received her Master’s in Somatic Psychology from the California Institute of Integral Studies in 2009.

There are 7 references cited in this article, which can be found at the bottom of the page.

This article has been viewed 33,348 times.

In the age of the internet, it’s easier than ever to connect to people we don’t know. When you spot a cute stranger online, asking them out is a little different than asking someone out IRL. We’ve compiled some tips to help you (hopefully) get a date with the person of your dreams.

How to ask a stranger out online

Maya Diamond, MA
Relationship Coach Expert Interview. 17 January 2019. Put up some quality photos of yourself in different scenarios so you look fun and interesting, too! [2] X Expert Source

Lisa Shield
Dating Coach Expert Interview. 13 December 2018.

  • This goes for any online platform, whether it be an online dating profile or just one of your social media accounts. If your profile looks boring or doesn’t have anything on it, your potential date might not want to go out with you.
  • It might also help to check out the other person’s profile before sending a message. That way, you have a little info on them before you start chatting.

How to ask a stranger out online

How to ask a stranger out online

Lisa Shield
Dating Coach Expert Interview. 13 December 2018.

  • “How long have you been rock climbing?”
  • “How’s your day so far?”
  • “What do you get up to on the weekends?”

How to ask a stranger out online

Maya Diamond, MA
Relationship Coach Expert Interview. 17 January 2019. You could talk about their personality, their hobbies, or even their career path. Stay away from anything about their physical appearance, though, as that can be a little bit creepy. [6] X Research source

  • For instance, you might say, “I really like chatting with you! I feel like we could talk about anything.”
  • Or, “It’s so awesome that you’re into snowboarding. All your videos look so professional.”

We all know referrals are the best way to get jobs. If this is new information to you or if you don’t know what referrals are, read Actual messages you can send to get referred into a tech company.

As I’ve been working with more students going through the job search, I’ve collected more data points on what types of messages work well (or don’t) for getting referrals.

Let’s talk about the cold message, which is when you contact someone you don’t know who works at a company you’re interested in. This is the toughest message to send. You’re literally reaching out to a stranger who is probably busy and isn’t asking for random people to contact them for help to get a job. Not only that, you don’t want to come off as annoying and of course this leads to fear of ruining your chances at the company you’re most interested in.

But keep this mind: anyone who’s held a corporate job for more than a year and especially for those in the tech industry, they know that cold emails or LinkedIn messages asking to “set up a phone call to learn more about [Company X]” is normal. I guarantee they’ve done it themselves and might even be the way they got the job they have right now!

However, even if cold messages are normal and even expected, they can be annoying.

Use the following message template to avoid being annoying when reaching out to someone you don’t know with the intention of asking for a referral.

How to ask a stranger out online

Cold message template

Hey [Name],

My name is [Your name] and I saw this [name or role and insert link to the job posting] opening. I’m really interested in this role and all that is going on at [Company]. I read about [mention some positive news about the company from their blog or press article], it sounds like it’s an exciting time and there’s a lot going on! I’d love to chat with you more about [Company].

A little bit about me:

  • I’m currently a [your role at your company]. I’m responsible for [describe what you do]. *(See below if you’re currently in between jobs)
  • Previously, I was a [role at previous company]. In my time there I [describe what you did]

I’ve attached my resume for detailed context.

Would you be for up for a phone call in the next couple of weeks? If so, I can send over a handful of time slots.

Your name

This is a good cold message because it shows you’ve done research on the company, introduced yourself without overwhelming a stranger with your life story, and specified a request. As an added bonus, you’ve agreed to take on the hassle of coordinating times to chat.

The template is in email format, but you may not have someone’s email address for a cold message. If that’s the case, reach out with this message through LinkedIn. If you do, break up the template message into a few messages so you’re not sending a wall of text over LinkedIn.

If someone writes back to your cold message, they may or may not be willing to talk to you on the phone.

If they’re open to a call, send over a handful of time slots to try to make it easy for them to find a time that works for them. Make sure you do some research to ask good questions about the role and company before you get on the phone. After the call, send a follow up email to thank them for the call and ask for a referral.

Here’s a good way to craft the sentence to directly ask for a referral:

If you have time and are willing, can you help submit my resume for the [role – include link to job post]?

If after the first cold message you get a response, but a phone call doesn’t work for them, they may reply back with, “What questions can I answer for you?” If this happens, send over a few, specific questions over email. Once you get a response to your questions, send a follow up thank you email and ask directly for a referral.

*In the template above, I have a bullet point describing your current job. If you aren’t at a company right now, mention the productive things you are doing that’s relevant to the role you’re going after. This could be an online course you’re taking, volunteer/consulting work, side project, etc.

Don’t be afraid to ask, you’re only holding yourself back

If you’re getting gun shy about sending a cold email because you don’t want to come off as an intrusive nuisance, don’t be. Everyone who successfully finds a job in tech does this!

I’ve always been surprised by how helpful people who I don’t even know have been in my career. It all started out with a cold message. So don’t be afraid to take the first step to reach out to someone (but don’t be annoying!). You’re only getting in your own way of the job you want if you don’t ask.

We think people don’t want to get into the deeper conversation, but when we skip small talks and ask some worthy questions people don’t mind open up their heart and connect with humanity.

We often sum up our conversation in small talks, we never think of asking worthy questions that directly touch the heart.

Well, deciding what question one can ask is the call of the situation. You are on a date and trying to impress, you probably cannot prompt up to philosophical talks, a combination of humor, sense, and smartness will prove your best bet there.

The simple formula to talk smart and ask worthy questions is to acknowledge the situation. You are in a funny mood and the person sitting next to you is more than serious, you certainly not going to make a good talk.

Some questions bring up sensitive material. You are going to listen to their fear, missed opportunities and intimate things of life, be compassionate, show sensitivity and where you need to smile don’t hide, pass a sweet smile and try to be happy.

Asking questions on the date and patiently listening make you a good choice of people. These are questions that ignite stimulating, thought-provoking and personal conversation and help to build a deeper connection with people.

You should better ask in a genuine or in conversation tone, one shouldn’t think you’re interviewing.

Even some questions can start a healthy discussion. Ask your friend your loved ones and find the interesting answer:

How do you spend too much time doing?

Introductory question! Get an insight into their daily life.

How they pass their time or how they make their every second count.

What is a new habit you want to form or quit?

We often try to adopt some good habits or quit some bad ones.

You will have a better understanding of their nature.

Where would you like to travel, now?

By knowing you come across their destined happiness associated with the place.

You may open discussion about traveling abroad, world cuisine, holiday destination, common interest, short trips and many others.

What is the craziest thing you have ever done in your life?

This overarching question is ambiguous enough to be a great question anytime.

Beware! You are about to enter into an introspective conversation.

Get ready to see the wilder side. The question leads to an engaged conversation.

What one thing you would like to tell me about yourself?

One of the most interesting questions:

You probably gonna hear the best or the worst thing about them.

What is the most spontaneous thing you have ever done?

It could be funny, courageous, and even stupid.

You may know their different side of personality.

What words of wisdom would you pass onto your childhood self?

Unique, attention-grabbing question tells a lot about the person.

It can be their biggest regrets, life lessons, amazing things they did in past, or any opportunity they missed.

What one thing you like to do in a day that makes your whole day happy?

Can be hard to answer!

This interesting question shows zealous nature and how they live their life to the fullest.

Which is your all the time favorite book?

Book, music, movie tells a lot about people.

Literature has its own importance in life.

What set you back in life?

The highly personal question should be reserved for closed ones. Strangers may not be comfortable revealing such deep introspections.

Hold them in your comfort zone and then ask personal questions.

Who is your idol? Do you want to be a copy of him?

This is the quintessential question, ask someone whom you want to open up.

We often emulate our idols or heroes and install their values in our mind app.

What single message do you want to give before you leave your life?

This is extremely deep!! Some may not have thought of this earlier.

The answer will show the essence of their life and the ultimate aim of living.

Don’t prompt up to this question initially, give people time to frame a comfort zone around you.

Do you believe in heroic deeds? What would it be?

Heroism, strength, and other personality trait question evoked by this lighthearted question.

If you have a superpower how would you use it?

But you can glean a bit of personal truth and desire from someone.

What is one thing you want to change the word?

Get to know whether the person is thinking about whole humanity or only himself.

If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

The answer will tell you how the person finds their healing power.

What is one thing people often misunderstand about you?

Awaits interesting replies!

See what others think about him which he thinks is wrong.

Do you believe in self-realization or just want to enjoy life without any thought?

The question reflects a deeper perception of the self “realization, and how he sees life.

How to ask a stranger out online

Last week, I got two emails. On the surface, they were very similar—both messages were from aspiring writers I didn’t know, both were polite and professional, and both were requesting advice and potentially an introduction to my editor.

However, my reaction to the two messages was very different. I was eager to help the first person and annoyed at the thought of assisting the second.

I couldn’t figure out why, until I went back and reread the messages.

The only distinction? The first person explained why she was asking me specifically for help—and I was flattered as a result. Meanwhile, the other person made his request with no explanation.

So, what can you learn from this to make sure you’re in the first camp?

Identify the Reason

Most of us request favors from strangers at some point (if not often) during our professional careers.

And we never pick the recipients of our asks randomly. There’s always a concrete reason we’ve chosen someone, whether it’s because he or she has the right expertise, works at the right place, or knows the right people.

But our mistake is assuming that our “why” is implied. However, this “why” is actually really important, as it gives you a chance to compliment the recipient while providing some context.

Include the Reason

Next time you’re asking someone for help (whether he or she is a stranger or not), make sure you provide an honest yet gratifying explanation of why you’re reaching out.

Let’s break down the two most common reasons.

You’d Like the Person’s Advice

  • “I’m looking for insight into [topic], and since you’ve got such a strong background into [field], I thought you’d be the best person to ask.”
  • “Your impressive LinkedIn profile makes me believe you’d give great feedback on [topic].”
  • “I’ve been stumped by [problem] for a while; I figured that since you’re an expert in [subject], you might be able to offer some help.”

You’d Like to Know More About a Company

  • “Because you’ve been with [employer] for [length of time], I’m confident you’d be able to give me a really thoughtful, accurate representation of what it’s like to work there.”
  • “I know you only joined [employer] [length of time], but since you’re working [in the department I’m interested in, in a position similar to the one I’m applying to, with people I’ll be working with], your description of how it’s been so far would be incredibly helpful and relevant.”
  • “As a [job title] for [employer], you clearly have a lot of influence, and I’d absolutely love to get your thoughts on the culture, values, and work style.”

Put it Together

So, after you’ve clarified why you’re emailing that person specifically and found the right way to phrase it, it’s time to weave your explanation into your request. Your best bet is using this template:

Introduce yourself + make your request + provide your reason

Here’s what it looks like in action:

I’m a freelance web designer who’s looking to transition to a full-time role. Since you’ve got a fantastic reputation in the design community and have worked with many of the agencies I’m interested in, I was wondering if I could get some advice about making the switch. Would you be available for a quick phone call or answering a few questions over email?

If you’ve got too much on your plate, I completely understand.

Now that you’ve got this trick up your sleeve, your requests for help should definitely be more successful.

Today, I’m delighted to say that our blog has been hijacked by the very cool dating expert, Claudia Cox. She is the author of ‘French Seduction Made Easy‘ and is passionate about sharing her expertise on communicating well in relationships especially via flirty texting. She runs the website textweapon.com where she makes the art of seduction look easy peasy. If you haven’t already, head over there and check it out. Over to Claudia for some savvy advice on how to keep that online chat going in the right direction.

Keeping an online conversation going

So you’ve passed the awkward “first contact” stage of online dating. You sent the first message, they replied – congratulations, everyone is onboard and ready to roll!

It can be hard to keep a conversation going with someone you don’t know YET, and who isn’t sitting across the table from you. You want to come off as fun, interesting and flirty, while also being considered serious, smart and trustworthy, right?

Aie, aie, aie… That’s quite a big task to accomplish using just a few messages to and fro! And you know what makes it even harder? Is that you don’t know what makes them tick yet – or even if it’s worth finding out…

If you find yourself stuck one message in, and you want some advice on how to spark up an interesting conversation that will tell you whether this person is worth getting offline for, read on.

1. Ask questions

Pretty much everyone loves talking about “numero uno” – so give your partner an opportunity to start gabbing away! Asking light, simple questions is a sure fire way to keep a conversation going online. The more they answer, the more fuel you’ve got for the conversation. Even better, you’ve just won some major points by flattering their ego (even if it’s just a little).

It’s also a good indicator for knowing if you have found a worthwhile match or not. “How so” you say? Well, if after asking them a mountain of questions, they still haven’t asked you the basics, you can be pretty darn sure they are self absorbed, and not the least bit interested in finding out what you’re all about. Time to move on, nothing to see here folks!

Keep it fun, it’s not a job interview – make your question a little quirky and different. This way you stand out from the rest of the “fishies” and get a better reaction – and please, don’t ask something they’ve already answered on their profile.

2. Get your flirt on

Flirting is fun, but when you’re doing it online you need to be slower about it than normal. Because your partner can’t see you, or the signals you’re sending, flirting too early in an online exchange can be a huge turn-off. Don’t immediately start talking about adult toys or send her a “selfie” at the gym all pumped up post workout. Make sure that you add just a lick of sass to your pre-meet up messages.

Going back to the good old questions, instead of asking him or her something dull such as “what did you eat for lunch?” give your questions a hint of spice. Ask “Why are you a cat person when everyone knows that dog people make better lovers?” Or poke fun at their answers in a flirty way (“Oh, you’re a Star Wars fan? Bet you’ve got Darth Vader pillowcases J”).

Make sure you don’t go overboard. Nothing kills a conversation early on like pushing boundaries waaaay too far (like being outright mean or vulgar).

3. Be honest

When you’re messaging almost anonymously, it can be easy to exaggerate or outright lie to make yourself look better. Don’t do it! One, because it will get awkward if you ever do meet up, and two, it’s human (and often endearing) to have flaws – embrace them, and your partner will too.

If you’re not proud of your height, say, “I’m short, but what I lack in height, I make up for in over-confidence.”

Make your flaws into a joke that you can both laugh about – they’ll be more likely to share theirs, so you don’t get any special surprises when you end up meeting.

4. Know when to take it off (line)

Even if you’re enjoying the online messages, don’t push your luck. Know when to take your virtual relationship offline before it fizzles out. After all, dating is about meeting up face-to-face, hearing their voice, drinking in their smell and feeling their touch.

In my experience, it’s best to meet up earlier rather than later – like before you know everything about each other, and you still both have an air of mystery about you. After all, you want your first date to feel like a first date, not a 10 th wedding anniversary, right?

Online conversation debrief:

Before jumping straight into it with the great advice you’ve just received, commit to memory the following “do’s and don’ts” of online conversation:

For the ladies:

Don’t be negative. Opening up with “I’m so sick of online dating…” makes you seem unenthusiastic… and also like you’ve been doing this for way too long.

Do be complimentary about his photo. Don’t make any jokes about it being photo shopped, the male ego is an extremely sensitive thing!

For the Gents:

Don’t go there. Seriously, men are the worst offenders here – don’t talk about the size of ANYTHING until you at least know what her favorite drink is (and have bought her a few)!

Do keep it light and fun. Don’t write long essays about yourself, which seem extremely interesting to you, but might not be all that easy to reply to. Stick with light, flirty topics that keep engagement levels high.

Well, there you go! 4 tips for keeping the online conversation going like a champ until you meet up in the flesh. Happy online dating!

How to ask a stranger out online

How to ask a stranger out online

Amy Morin, LCSW, is the Editor-in-Chief of Verywell Mind. She’s also a psychotherapist, the author of the bestselling book “13 Things Mentally Strong People Don’t Do,” and the host of The Verywell Mind Podcast.

How to ask a stranger out online

Some people can strike up a conversation with anyone–even complete strangers. But many others find it difficult to talk to a stranger. This can be particularly stressful if you have social anxiety disorder (SAD). But even if social small talk is hard for you, it is possible to improve your conversational skills and feel more comfortable talking with strangers. The best way to do this is to practice.

Your initial goal is to make an introductory statement, which does not have to be complex. The point of that first comment is to open the door, and to give you the chance to say something else once the person responds.

Comment on Something Personal

You’ll find that everyone you meet has something unique about them—an item of jewelry, an unusual shirt, or even a tattoo. These tell a story about a person. When you notice and compliment them, it can give you a starting point for conversation.

For example, you could initiate a conversation by saying:

  • “Wow, that is a beautiful pendant. What kind of stone is that?”
  • “Nice shirt! You’re a Grateful Dead fan?”
  • “Is that a tattoo of Yoda on your shoulder?”

Avoid commenting on intimate aspects of a person’s appearance—such as asking, “Is that your real hair color?” or “Wow, you must work out a lot!”

After you receive a response, make sure you have something else to say. That will give you a common platform on which to build a conversation and, ultimately, a relationship with the person you’ve just met—even if the relationship only lasts a few minutes.

Offer a follow-up story that reveals a bit of personal information about you. For example, when the person responds to your initial question, you could follow up with something like:

  • “I saw a pendant like that at a bazaar in India.”
  • “My father was a real Deadhead. He took me to see them when I was a kid.”
  • “I love tattoos. I’ve been thinking of getting one but I’m not sure what to get. How did you decide on Yoda?”

These statements will help connect you to the person and keep the conversation moving. Remember, the goal is not to say the perfect thing or come across a certain way, but to keep talking.

Ask If You’ve Met Before

This classic conversation starter can work in the right circumstances. If you say to someone, “You seem really familiar, do I know you from somewhere?” it makes it easier to gather and give information and keep a conversation going.

For example, if you ask someone where they went to high school and it turns out you went to the same school, you could follow up by offering a fact like, “I was in the marching band. Did you play an instrument?”

If you ask someone where they work and realize that you have seen them there, it gives you the opportunity to make a connection, “I love that Starbucks!”

As the other person is giving information about themselves to you, it’s OK to go off on interesting tangents. Remember: the goal is not to find out if you’ve met before, it’s to get to know the other person.

Break the Ice With Humor

Another great way to start a conversation with the people around you is to simply comment on your shared surroundings. A little humor works great here.

For example, if you are sitting in a lecture hall and notice that your professor looks familiar, you could say to the person next to you, “Doesn’t he look a bit like Harry Potter?”

Keep your commentary positive—never mean-spirited or judgmental. You want the other person to feel comfortable getting in on the joke with you. You could follow up on your previous comment about your professor with something like, “I wonder where Hedwig is?”

Humor is difficult with someone you don’t know well, which means using this method to start a conversation can be risky. However, if you do find someone who shares your sense of humor, it can be the start of a great friendship.

If you don’t receive a positive response from one person, the method might work with someone else. The more you practice, the easier it will be to talk to a person you don’t know. With time, you’ll become more confident and won’t need to rely on tricks to get a conversation started and keep it going.

Keep the Conversation Going

You might participate less in a conversation because your anxiety makes you too uncomfortable and self-conscious or because you don’t have experience making conversation. But a 2016 study showed that people with social anxiety tend not to contribute equally to conversations. As a result, they are less well-liked than others.

So it’s important to hold up your end of a conversation once you start it. Many people can do this with people they know, but they are self-conscious with strangers. Their anxiety holds them back and prevents them from being their true selves.

Cope With Conversation Challenges

Lacking certain social skills can inhibit your ability to engage others in conversation, especially if it makes you seem unfriendly. For example, research shows that people with social anxiety tend to make less eye contact during conversation.

Working on making and keeping eye contact when you are talking to others will help you appear more approachable and friendly. This will make it more likely people will respond to your attempts to start a conversation.

If you feel that you don’t have the social skills and experience needed to be a good conversationalist, self-help books and working with a therapist can help you develop them.

While it’s important not to avoid conversations with strangers because they make you feel anxious, your safety also matters. Practice talking to strangers in safe, public environments where the stakes are low. And if you are chatting with someone online, always protect your personal information.

A Word From Verywell

Strategies for starting a conversation and being more comfortable around others will work best if you are able to work on and manage your underlying anxiety. With time, practice, and the right treatment, you can gain confidence and improve your conversation skills. If you have social anxiety, you might find that treatment with cognitive-behavioral therapy or medication helps you feel more at ease in social settings.