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First Date Tips - How to Ask Someone Out

Updated on May 13, 2017

Sometimes you have to make the first move, and here is advice on how to do it.

Maybe you have secretly really liked a special someone for a little while, and now it's time to take it to a new level, and ask him or her out on a date.

Or, maybe, you have just met someone, and want to seize the moment.

How do you do it? How do you ask someone out on a date for the first time?

At a Glance

  • Observe and learn
  • Look your best
  • Appear confident
  • Expect a 'yes'
  • Avoid awkward
  • Stay positive
  • Tailor your approach
  • Use the ideas below

Before Jumping In ...

There are a few things you should consider before you ask anyone out. Some of these you can think about now, so that you are prepared.

The more you feel in control, no matter what the outcome, the more confident you will be ... and the right level of confidence is attractive!

Observe your potential date.
Yes, of course you've been doing this already, but I mean observe in a more logical way. There are questions that you can never just ask without giving completely the wrong impression, so you need to be quietly observant. You can learn a lot about a person just by keeping your eyes open, and without resorting to stalking. Things to look for are:

Is the person already attached?
Asking someone out who is clearly already in a relationship is generally not a great idea (especially if the other half is present at the time!).

What is the person's orientation?
He or she might never be into you, no matter how attractive you might be. It may not be immediately apparent, but at least be aware if there are signs.

What are the person's likes or dislikes?
Any information will help you once you approach the person. Initially you can look for clues in fashion, people they are with, places they go and so on. If you know the person a bit better, you will be able to arm yourself with more details.


Look your best
If you are feeling good about yourself, it will help you feel more confident. What's more, first impressions really are important. It takes quite a number of positives to cancel out a negative first reaction, so it's best to aim for positive first impression.

You never know when the opportunity might arise, so if you are looking for a special someone, it's worth putting a bit of effort into yourself.

Of course, having said that, some of the best relationships have started when two people look their absolute worst.

However, as a general rule, if you like and are happy with how you look, chances are, that special person will too.

Expect the person to say yes.
If you ask someone out with the expectation that the answer will be, "no", then that will be the most likely outcome.

If you ask as though you expect the person to accept, it will give you an air of confidence and experience, and make the person more likely to say yes.

This doesn't mean you should be cocky. Overconfidence, even when it is compensating for shyness, comes across as arrogance.

Just having a positive attitude will greatly improve your chances of getting that date.


Allow Someone To Politely Say No
Be aware of and understand subtle hints. Avoid cornering the person into having to openly reject you.

For example, never, ever ask if someone is free first. Even asking what someone is doing over the time of the planned date is a mistake. It takes away the opportunity for the person to make a polite excuse, and will make things very awkward.

You: What are you doing on Saturday night?
Potential Date: Nothing much.
You: Great! Would you like to go out?

You: I'm going to a party on Saturday night. Would you like to come?
Potential Date: Sorry, I have something on that night.


You: Would you like to go and have dinner some time?
Potential Date: Um, that might be nice.
You: How about Saturday night?
Potential Date: Sorry, I have something on that night.

Awkward moment avoided.

Remember, if the person is interested in dating you, he or she will always suggest an alternate date if he or she really is unavailable for the time you are suggesting.

Be prepared for rejection.
It happens. Often. Dating is a sensitive and immensely subjective game. Rejection is never easy, but it really shouldn't be taken personally. Remember - every single person, no matter how amazing, has been rejected at some stage.

The best way to cope with rejection is to be prepared for it. Play out possible scenarios in your head where the person says no, and plan how you will react.

Your most dignified option is accept the rejection with politeness. Show you are mildly disappointed, but that you are okay with it. Especially with someone you will see again, make sure that you are clear that this will not affect your existing friendship. You could say something along the lines of, "Okay, that's fine, it was just a thought," and smile. Then, as soon as possible without being obvious, move on. This could be physically if it's someone you just met, or by changing the subject if it's someone you already know.


How Well Do You Know the Person?

How you approach the first date will depend on how well, if at all, you know the person.

Normally, you can divide this into three categories: the person you just met, the person you already know, and, the friend.

How To Ask Out Someone You Just Met

Often, with someone you just met, you have to act immediately, as you might not have another opportunity.

Your best approach is to:

  • Make contact with your eyes. This will help you gage interest.
  • Approach the person and strike up a conversation. Do not use a "pick up" line unless it is extraordinarily clever and original (most aren't). Usually a simple question or comment about wherever you are meeting is sufficient.
  • If the reaction is positive, strike up a conversation.
  • Show the person that you are interested in what they have to say.
  • Suggest meeting up somewhere else so you can get to know him or her better.

How To Ask Out Someone You Already Know

Asking out someone you already know carries a little more risk, but if done diplomatically, it doesn't have to be awkward.

  • Consider how you are going to ask. I personally think that all date invitations should be person to person, or at least with a phone conversation, but not everyone thinks like me. Today there is always Facebook, texting and so on. The advantages of asking someone out in person are that you can immediately gage the reaction, and control any awkwardness that might result. Impersonal invitations can and do work, but if they go wrong, there is a lot of room for misinterpretation and miscommunication.
  • Think about what you believe the other person would like to do.
  • Start with a conversation.
  • Suggest it might be nice if the two of you meet up sometime.
  • If the reaction is positive, suggest a definite day and plan, such as coffee tomorrow afternoon, or dinner on Saturday night.

How To Ask a Friend On a Date

Moving a friend into the dating zone is probably the most difficult, as you have the most to lose if it goes wrong. On the other hand, you already know more about this person, and you already know that you really like them, so in some ways it's much easier.

Approach this in the same way as you would with someone else you already know (see above).

Be aware that your friend might not realise that the occasion is actually a date.

Once accepted, take advantage of the time you are together to gently hint that you are interested in taking your friendship to a different level. Carefully monitor the reaction at all times, and if you receive any negative vibes, pull back to just being a friend.

You Are Not Alone

Everyone has to deal with the difficulties associated with dating at some time or another.

Hopefully, for you, the outcome will be positive, but if not, don't give up. Try to stay relaxed and confident.

Every person is different, so never take rejection personally. Just dust yourself off, and try again. There is someone out there who will think you are just perfect for them.


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