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How to Introduce Yourself to Single Women

July 16, 2021
How to Introduce Yourself to Single Women

OK, so we appreciate that there are single men and women out there looking for dating advice, as well as non-binary genders. 

Still, for this guide, we're focusing on guys as the largest online dating users, who most often contact us for help with working out how to break the ice!

How Do I Know if a Woman is Single?

The first issue we'll start with is how you know a woman is single at all. It's a vital consideration if you want to begin a conversation with someone out and about - because it's extremely easy to put your foot in it and potentially end up with a disgruntled husband on your tail!

In short, if you're unsure, approach the situation as if you are being friendly. Never, ever try a sexy pick-up line (they're almost always terrible!) and be prepared to back quickly away with a polite apology if the person in question indicates they aren't interested. 


  • Not all married women wear rings.
  • They might not be interested in men.
  • You can't tell from appearance if someone is single.
  • A sexy outfit doesn't mean they're looking for attention.
  • Attached women go to singles bars with their friends.

Of course, the only sure-fire way to know you're only trying to pluck up the courage to chat to a single person is to join an online dating site, where each and every member is looking for love!

If you've not tried it before, then trust me, it's a whole lot less stressful than trying to make a flirty conversation in a crowded bar or convince a stranger you're genuinely interested in getting to know them.

For recommendations of the best dating sites depending on what sort of relationship you're looking for, check out the top 10 lists on Best10.

What's the Best Way to Start a Conversation with an Attractive Stranger?

These are the basic rules of thumb I'd advise thinking about before you head off into the sunset armed with some one-liners.

  • Ask a question. Launching into a monologue about what a great guy you are never works. Not on a dating site, not in a park, not ever. Asking something is a gentle way to invite a woman into a conversation with you - and if they don't answer, they're making it clear they don't want to engage. No harm, no foul!
  • Be honest and authentic. It's totally OK to feel nervous about introducing yourself to a gorgeous woman who is everything you've ever looked for! If you are tongue-tied, then say so - it's so much more attractive than fake bravado! Try, 'Please let me know if you're not interested, but do you mind if I buy you a coffee? I'm a bit nervous about talking to you!' Again, she can say yes, and you're golden - or say no, and you haven't embarrassed yourself or made her feel uncomfortable.
  • If you know you have something in common, always lead with that! Say you've matched with someone online, or you're at the same comedy gig or concert, you already know they like something you do too. It's a perfect way to find a mutual interest, so perhaps 'I thought xxx was amazing, what were your thoughts?'
  • Think about your body language as well as what you want to say. It's vital to remember that women are smaller than men in most cases, and most have experienced discomfort when feeling cornered. Don’t get too close, don't try to be macho (which can feel physically intimidating!) and don't shout - if it's too noisy to be heard when talking normally, it's not a good time.

These are general guidelines to think about, but of course, you can go freestyle if you have a perfect way to introduce yourself! 

It helps to be a natural comedian, but we can’t all be great at chatting up strangers. Take a few deep breaths, calm your nerves, and go for it without any pressure, and you'll be just fine.

Also Read: How to Have a Successful First Date With a New Guy

What's the Best Way to Introduce Myself to Women Online?

Now, the online dating scenario is a little different. For starters, you already know that a person you want to chat with is single, so there aren't so many considerations there.

Also, you usually have a few features and games to find out whether you're likely to be compatible in the first place! For example:

  • If you've come across a woman through a mutual like game, they have confirmed they find you physically attractive, so there's a better chance of success.
  • Searches allow you to filter by all sorts of parameters, and you can look for singles that live nearby, are of a similar age, and share some of your hobbies.
  • Looking for profile information is really worth looking at. Most dating site singles will have a status or some preferences to give you a quick insight into whether you're likely to be their cup of tea - and, therefore, whether it's worth getting in touch!
  • Icebreakers are an excellent option. These are pre-written messages you can send, which take the nerves out of thinking of how to start your message.

If you are completely lost for words, you can also consider sending something other than a written message! Most dating sites allow you to send winks, likes, hearts or virtual gifts - depending on what sort of app or service you’re using.

I'd say, though, that where these features are free, it's not uncommon to get tonnes of them per day, so if you're feeling confident enough, follow it up with a direct message to make sure you stand out from the crowd.

Last but not least, don't sweat it too much. I hear from so many men who feel nervous about speaking to women because they have been rejected horribly in the past. 

My advice would be that if you are polite, respectful and friendly and a potential date puts you down for making an effort, they're not the kind of woman you want in your life anyway.

Good luck!

Lauren Edwards-Fowle
Lauren Edwards-Fowle
Lauren is a freelance writer passionate about how we develop rewarding experiences, and overcoming the barriers we face to living our best lives. Lauren writes regularly about the modern world of dating, relationships, parenthood, and social dynamics.