How to Ask a Woman on a Date without Making Common Mistakes

Co-authored by Stefanie Safran

Asking a woman out on the first date can be a scary and potentially frightful thing sometimes. You don’t know if you’ll be rejected or if she’ll accept your invitation out. You’ll also be nervous about how you look, how you talk, and how you come across. Unfortunately, many men make a lot of common mistakes that blow their chance at a first date before they’re even on a date. Fortunately, though, there are some ways to increase your odds of getting her to accept your invitation instead of turning you down.

Part 1

Part 1 of 3:

Communicating Your Interest

1
Ask her out in person, if you can. Asking her out in person is key to successfully getting a date. Although you may be shy or intimidated, you can’t let those feelings rule you. A date is a potentially intimate moment when two people get to know each other a little better. You should start it off that way.^{[1]
X
Research source}
2
Pick the right time and place to ask her out. If you’re going to ask her out in person, pick the right time and place. Picking the right time and place to ask her out is one of the most important things in getting a date. You don't want to ask at the wrong time or place, or you might blow your chance. There are a number of things you should consider when asking her out in person:
- Don’t pick a time or place where she is distracted.
- If you’re in a bar or club with friends, try to find a moment when you're alone. Otherwise, some of your or her friends might invite themselves and make it a group date.
- Don’t ask too early in your encounter. Ask toward the end of your encounter when you think you will part ways. Otherwise, you might seem too desperate.
Advertisement
3
Call her with confidence. Perhaps you got her phone number at a club, and want to contact her the day after and set up a date. This is alright, but make sure your phone call and texting is confident and pleasant. You’ve done the hard work of making first contact and getting her number, don’t blow it now.
- Start off the conversation in a light way. Joke about something (appropriate). Try to get her laughing or relaxed.
- Demonstrate your interest by asking her questions, but nothing too prying. Focus on light things.
- Invite her out. Tell her you’d like to get to know her better. Based on personality, you can ask her to suggest something, or you can suggest something you think she likes.
- If she declines, she might tell you why. If it’s a scheduling issue, ask her when a good time is for her. If not, drop it and politely end the conversation – unless you want to pursue a friendship.
- If she accepts, try to end the conversation politely.
4
Text concisely. Texting might be a way to follow up with her after you met the night before. It is a noncommittal way to communicate that many people are comfortable with. However, there are a number of things you can do wrong that will blow your shot at getting a date.
- Consider texting her the afternoon after you met her. By avoiding an immediate text, you're showing that you're thinking about her, but you're not obsessing.
- Start off with a light or humorous comment that will relax her and remind her of who you are. For example: "Hey! Remember that devastatingly handsome guy you met last night?"
- Don’t write a long message to her.
- Instead, be clear, concise, and articulate what you want – a date with her. For example: "I'd like to take you out so we can get to know each other better."
- Don’t be forceful. Avoid telling her what she should do or what she'll be missing if she does not go out with you.
- Allow her time to respond. Don’t jump the gun if she doesn’t text back in 3 minutes and then shoot her another text. Wait a few hours or more. Chances are, if she wants to go out with you, she’ll respond.^{[2]
  X
  Research source}
5
Avoid being vague about when and where you’ll go out or meet. The last thing she wants is to date a guy who is wishy-washy about what he wants. Be clear about when and where you'd suggest meeting.^{[3]
X
Expert Source

Stefanie Safran
Dating Coach & Matchmaker
Expert Interview. 8 May 2020.} Feel free to ask her opinion, but if she defers to you don't worry about it. Pick where and when you want to go, and set the date.
- Set a specific time.
- Set a specific place.
- Let her know where you'll be going and what you'll be doing so she'll be prepared.^{[4]
  X
  Research source}

Part 2

Part 2 of 3:

Treating Her Appropriately

1
Treat her with respect. Make sure that any interactions you have with her are respectful and not overbearing. Don't assume that women want to be the lesser party in the relationship and always defer to your judgement. Rather, assume that your relationship, if it goes forward, will be one of equals and one based on mutual respect.
- Never insult her or be rude to her.
- Always consider her opinion and taste.
- Don't make assumptions about her before you get to know her.^{[5]
  X
  Research source}
2
Avoid looking like a stalker, and know when to give up. Even though you're really into her, you've got to avoid looking like a stalking. Don't obsess, and if you do, try to control it. If she's interested in you, she'll let you know. If she turns you down, then call it quits.
- If she rejects you, don't try to read in between the lines and interpret it as her playing "hard to get."
- If she rejects you, don't go out of your way to "bump" into her randomly.
- If she rejects you, don't be rude. Just move on.
- Once she has ended communication with you, it's over.
3
Be honest about your feelings. Don’t sell yourself as a “friend.” When asking her out, don’t approach her as if it is two friends doing something fun. If you want to date her in a romantic way, be clear about that. If you're not clear, you're simply luring her into a friendship with ulterior motives. This is something that will ultimately frustrate both of you.^{[6]
X
Research source}

Part 3

Part 3 of 3:

Presenting Yourself in a Positive Light

1
Make sure you have positive body language. When asking her out, the tone and language of your body should match up with your words. You want her to get the sense from how you’re carrying yourself that you are confident and want to get to know her a little better. Make sure you’re standing up straight, smiling, your shoulders are up, and your hands and arms are in a relaxed and non-defensive posture. There are several things you should avoid:
- Slouching over.
- Crossing your arms. This demonstrates that you’re in a defensive posture.
- Fidgeting with your hands. Don’t play with things in your hands, and don’t keep your hands in your pockets.
2
Have good hygiene. In order to give her a good impression about who you are, you've got to maintain good hygiene and look well-kept. If you typically don't maintain good hygiene, now is the time to step it up. There are a number of things you need to do:
- Shave or groom your beard.
- Shower before a date.
- Use deodorant and cologne, if you want.
- Floss and brush your teeth.
- Wash your clothes and only wear clean clothes.^{[7]
  X
  Research source}
3
Exude confidence. When you ask her out, you need to make sure you seem ultra confident and sure of yourself. Try to think positively and focus on all of your good qualities in your own mind. There are pitfalls to this, though. Consider:
- You don’t want to come off as arrogant or full of yourself.
- You don’t want her to think that you think you’re too good for her.
- You don’t want to alienate her or her friends by bragging or boasting about yourself. ^{[8]
  X
  Research source}
4
Act naturally and don't make a big deal out of asking her out. Don't make it sound like asking her out is a matter of life and death. Avoid inserting a sense of urgency into the situation. Instead, act nonchalant, but interested. If you are tense and nervous when asking her out, she will feel just as tense and nervous. Make your invitation sound as if it was the most natural thing for you to do (and it should), and this will help her feel comfortable and at ease with the plan as well.
5
Resist the temptation to propose a grandiose first date. Proposing a grandiose date might give the wrong impression about who you are. While your first date should be memorable, you don’t want it to be the sort of thing that could intimidate her or could signal to her that you’re jumping the gun on a relationship that does not even exist yet. The purpose of the first date is to spend time together and focus on each other rather than some very interesting activity that would distract you from each other. Avoid:
- Anything that requires traveling more than a half hour from your home city. You both should feel at ease and at home wherever it is.
- Events like concerts or music festivals. Such events will undermine the ability for both of you to communicate and form a bond.
- Events that the other person might not be interested in. Don’t propose a date to an exhibition on modern art unless you know that she’s also passionate about it.^{[9]
  X
  Research source}
- Dates at locations that will force you to continue spending time together even if things go badly. Public spaces and settings are better because they will give you exit options.^{[10]
  X
  Expert Source
  
  Stefanie Safran
  Dating Coach & Matchmaker
  Expert Interview. 8 May 2020.}

Expert Q&A

Question

How do I keep her interested between dates?

Stefanie Safran
Dating Coach & Matchmaker
Stefanie Safran is a Dating Coach, Matchmaker, and the Owner of Stef in the City, a Matchmaking and Dating Coaching business focused on an honest and hands on approach. Stefanie labels herself as “Chicago's Introductionista®” as she has over 15 years of experience in the matchmaking industry. Her work has been featured on various media such as: ABC7, NBC5, CBS2, WGN, FOX, The Chicago Tribune, The Chicago Sun Times, The HuffPost, and Refinery29. She holds a MBA in marketing and branding from Loyola University in addition to her BA from the University of Wisconsin-Madison.

Stefanie Safran

Dating Coach & Matchmaker

Expert Answer

The most important thing is probably to make sure the initial dates go well. Women are very much looking at if you make an effort. Don't underestimate how important it is to be well-groomed, to have clean nails and hands, to dress a little more nicely than you would if you were just going out with buddies. Also, follow basic etiquette. Don't be on your phone when arrive, and don't sit and text during dates. Instead, be fully focused and paying attention to the person in front of you.
Question

How do you ask a girl out on a first date?

Stefanie Safran
Dating Coach & Matchmaker
Stefanie Safran is a Dating Coach, Matchmaker, and the Owner of Stef in the City, a Matchmaking and Dating Coaching business focused on an honest and hands on approach. Stefanie labels herself as “Chicago's Introductionista®” as she has over 15 years of experience in the matchmaking industry. Her work has been featured on various media such as: ABC7, NBC5, CBS2, WGN, FOX, The Chicago Tribune, The Chicago Sun Times, The HuffPost, and Refinery29. She holds a MBA in marketing and branding from Loyola University in addition to her BA from the University of Wisconsin-Madison.

Stefanie Safran

Dating Coach & Matchmaker

Expert Answer

Present a plan to her to see if she's interested. Try to phrase your idea for the date as something specific that you're open to her input on. You could say "What do you think of going to lunch at Mellie's, or would you prefer to walk in the park?"