How To Ask A Woman Out: Advice To Help You Succeed

Updated October 22, 2024by Regain Editorial Team

When there is a woman you’re interested in, you might feel compelled to try to ask her out on a date, but this can often be much easier said than done. Many people find it scary and nerve-wracking to ask someone out. You might be worried about getting rejected, and sometimes you may even be nervous about having the words come out wrong. But, with practice, patience, and some useful strategies in mind, asking a woman out is something you can feel more confident and comfortable doing over time. Read on for a few tips to consider if you’re having trouble asking someone out. 

Getty/AnnaStills
Asking someone out can be difficult

Tips for asking someone out

Get to know her

Getting to know the woman that you're interested in can be a helpful first step. It's not unheard of to ask a woman out before you know her very well, but it may feel easier to talk to her once you get to know her a little bit. You might want to spend some time talking to her to determine if there is any connection there before you go through with asking her out. After all, you might be initially attracted to a person and then find out that you two have very little in common. You can try to spend a bit of time together and show her that you're genuinely interested in her; this can give her a chance to pick up on your feelings, which may also make it feel easier to ask her out when you’re ready. 

Learn about things that she likes

Learning about the things that she likes can also be very useful. If you have a sense of some of the things she likes and doesn’t like, this can help you suggest a date that she might be more interested in. For instance, if you learn that she loves Italian food, you might suggest a great Italian restaurant for your first dinner date. Or, if you learn that she is a vegetarian, you might want to avoid taking her to a restaurant that is best known for its steaks. Perhaps she mentioned that she really hates horror movies, so you'll know not to choose the latest slasher flick if you're planning to ask her on a movie date. Simply talking to her a few times and continuing to get to know her can make planning out a potential first date a little easier.

Ensure that she's single

You may also want to confirm that she’s single before you ask her out. This way, you can try to avoid the potentially awkward situation of asking her on a date only to learn that she is already attached. It’s not always obvious if someone is in a relationship, so if her relationship status doesn’t come up naturally in conversation, you can simply ask. If you don’t feel comfortable asking her directly, you could think of more subtle ways to weave that into the conversation, such as asking if she has plans with a significant other that weekend. 

Getty/Vadym Pastukh

Think about what you want to say

You might also find it helpful to plan out what you want to say first before you ask her out.  You don't have to stand and practice a long speech in front of your mirror, though you can certainly do that if you think it would be helpful for you. It could simply be helpful to give a bit of thought to how you’d like to phrase your question. If you’re really nervous, you might also find it helpful to ask a friend for advice or ask them if you can practice by asking them. 

Be confident in yourself

Putting yourself out there can be scary and require some courage, so it can be important to feel confident in yourself. Feeling confident and having a healthy level of self-esteem can help you feel more at-ease when asking someone you like out, and it can also help soften the blow if someone turns you down. Confidence might appear in the way in which you speak, the words you choose, and maintaining eye contact with the woman you’re asking out. If you feel like you have low self-esteem, there are plenty of ways to try to boost self-esteem, such as challenging negative thinking, focusing on the positive, forgiving yourself, and spending time with people you love. 

Getty/Luis Alvarez
Asking someone out can be difficult

Plan something thoughtful

Suggesting a thoughtful first date can also be a nice touch. As mentioned earlier, learning the types of things that she likes and doesn’t like can be useful, and you can draw on this information when you are trying to think of a date she might enjoy. Rather than suggesting something vague, you could plan out something more specific and thoughtful based on what you know about her. She might be more inclined to say yes if it's obvious that you have put a bit of thought into planning a nice first date.

Be kind and respectful

Finally, remember to be kind and respectful. Even if you incorporate all of these tips and all the other advice out there, she may still say no. There is no way to guarantee that someone will agree to a date; sometimes, people are just not interested in us and not interested in dating, and that’s alright. Rejection is a part of life. If she turns you down, try to react with kindness, respect, and understanding. 

Online counselors are available to help

If you would like additional help in gathering up the courage to ask someone out, boosting your confidence, figuring out what to say, and navigating other dating and relationship concerns, an online counselor can help. In fact, research has shown online therapy to be effective for treating low self-esteem

Navigating the dating scene and figuring out how to ask someone out can also come with a lot of confusing moments and unexpected hurdles. In these times, it may be helpful to reach out for support in the moments when these concerns arise. With online therapy through Regain, you can reach out to your therapist at any time using in-app messaging, and they will respond as soon as they can. 

Takeaway

Asking a woman out can be nerve-wracking, but there are things you can do to feel more confident and comfortable doing so. For instance, it may help to get to know her more, learn about what she likes and dislikes, plan out what you want to say, and be confident in yourself. For further help with these and other dating concerns, you can connect with an online counselor for support.

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