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15 Tips: How To Ask A Someone Out

Dr. Lisa Lawless

Dr. Lisa Lawless, CEO of Holistic Wisdom
Clinical Psychotherapist: Relationship & Sexual Health Expert

finger puppets, man holding flowers for happy woman, how to ask someone out tips

Make Peace With Rejection Upfront

Make peace with the concept of rejection before you ask anyone out. This will determine the tone in which you ask someone out in the first place. If you come in with the attitude that it is alright if this person does not want to date you, your confidence levels will be reflected in that upfront.

Keep in mind that rejection may have nothing to do with you. People are going through their own life processes of grief, depression, low self-esteem, and stress. They may simply not be in the space to date you or anyone else. Sometimes they just know themselves well enough to know that the two of you would not be compatible. They are rejecting you to save you both future problems.

Remember that it is not an indication that you are not worthy of affection; rather, dating this person is not the right fit for them at this time. Rejection is part of life, and you have to learn to accept that some things are not meant to be and work toward something that is. Handle it gracefully and show them that even though they may not want to go on a date with you that you are strong enough to handle vulnerable situations with tact and poise.

Making A Good Impression

People are relatively good at assessing whether they want to go out with someone based on the first interaction. Here are a few tips for ensuring you make a good impression.

When To Call Or Text

Call or text in the evening. Like most people with day jobs, this is when they are most likely to be free to talk. Call or text after 8 p.m. to avoid interrupting dinner, but before 10 p.m. in case they go to bed early. If they seem busy or rushed, ask them if you're calling at a bad time. And if they say that you are, find out when a better time would be for you to contact them again.

Call From A Comfortable Setting

When you're comfortable and relaxed, it shows through in your voice. Avoid calling from the office or the car when you're stuck in traffic. Calling from these places is not only uncomfortable, but it's also distracting. Instead, call from a quiet room. You want them to know that they have your undivided attention.

Get Your Voice Relaxed And Clear

People like someone who sounds relaxed and confident. Tips to get your voice sounding its best:

  • Hum out loud with your mouth closed. This little trick can help you train your voice to stay relaxed right before a conversation.

  • Call standing up. Talking while standing up will also lend a richer tone to your voice.

  • Talk slowly. Take your time with your words. People sound nervous when they speak too quickly.

  • Consider masturbating before you call, you will be more relaxed, and your voice will reflect it.

Make Good Small Talk

It's natural to make small talk in a first phone call, but you can still try to keep the conversation interesting. Avoid cliché topics like the weather and politics, and focus instead on subjects relevant to both of you.

You also want to be mindful of talking too much about yourself as people notice these things. Actively engage them in the conversation by asking questions instead of just answering the ones they throw your way. Ask them about themself and what they have been up to since you first met, then let the conversation flow from there.

Just keep it light and easygoing. One item you should make sure not to delve into is past relationships. This is a touchy topic of conversation at any point in a relationship, and it's an incredibly delicate one during a first phone call. Talking about past dates that went sour or relationships where mistakes were made is a guaranteed downer.

Make References

Running out of things to talk about? Try using references to when you met or saw them to spark a new direction for the conversation: Was there a random song playing in the background? Did they post something interesting on social media? Was there something memorable that they said? Was there a funny incident? The possibilities are endless. Try to think of a few memorable things about the time you met or saw them beforehand to avoid those awful, awkward moments of silence.

Make Them Laugh

There's one thing nearly all people look for: the ability of someone to make them laugh. Try to drop a few jokes during the conversation to let them know that you have a sense of humor. But don't overdo it: you don't want to come off like you're doing a stand-up routine.

Don't Be Crude

Revealing your love of something like Mexican or Italian food can be a good topic. Revealing your love of porn right off the bat can be off putting. There's a fine line between being comfortable and crude, so make sure you keep the conversation tasteful. Don't put too much emphasis on framing yourself as high-class but someone who is safe and approachable. Pompous people can be just as insufferable as crude ones.

Propose A Specific Date

Make sure that you have an idea in mind for a date before you call. Remember, the ball's in your court, so you're going to be the one to hammer out the details. Be specific about a location and day you'd like to meet up. Where should you go? Grabbing a drink, coffee or meal together always makes for a casual first date, and you can consult one of the various local guides out there for tips on a good place to go. Be assertive, but have a backup plan. If they can't make it that day or don't like the type of place you suggest, then propose an alternative. If, at that point, they still refuse, ask them for a suggestion in an upbeat, non-defensive manner.

Once You've Secured The Date

Don't feel the need to keep the conversation going after they agree to a date. That's the primary objective of the first phone call. There will be plenty of time for deep conversation later on. You are probably going to be nervous so the less time you chat may be better unless you feel the conversation is going really well.

Group Activities

Group dates can be an excellent way to get to know someone, which allows people to feel a bit safer when they are going out with someone they have just met. While they are not as romantic initially, it can be a good experience for you to share so that when you are able to secure a second date, you already have shared experiences to talk about.

Asking them to join in a group activity also takes the pressure off the date question as it sounds like you already have plans and are simply offering them the opportunity to join in with you. It lets them know you are interested in them and can make any rejection easier because they are not rejecting you, they are rejecting the activity.

For example, in a text, it would look something like this: "Hey, my friends and I are going out to brunch on Saturday. You should come with us! Let me know if you are available."

Ask For Advice

When you first open up the conversation, consider asking them for advice, such as whether a restaurant is any good. You can even use humor around the question, such as saying, "I have a serious question for you... do you like the food at this restaurant or that one?" and laugh to let them know you are kidding around with them. Then ask if they would like to come with you to enjoy it.

Talk About Light Topics

Discussing things like favorite foods, restaurants, and fun activities can be a good way to start a conversation with someone. Again, using humor can be a beneficial tactic. Keep in mind that people have insecurities just like you do, so they will typically want to fill those awkward silences and keep a conversation going. If they are being quiet they may be sending you a message that they are shy or not interested. Try to keep the conversation going but if their body language or tone of voice is showing you they are not interested wrap up the conversation.

Read Body Language

If you are in person or talking on video, make sure that you read body language to give you cues about how comfortable or attracted someone is toward you and respect those cues. If they make eye contact with you, lean toward you, mirror your body language, make attempts to touch you, or demonstrate grooming behaviors (preening) where they adjust their hair or their clothing, they are showing you possible signs they are interested in you.

Honor Safety Concerns

If your date is concerned about safety, be completely open to any boundaries your date requests, such as meeting in public and arriving separately, having a group date, and meeting during the day. This is not about you; it is about them making sure they are safe. Showing respect for any boundaries your date wants without challenging them or trying to reassure them that you are a good person is essential. Just allow the boundaries because doing so shows them you are an understanding and good person, which speaks louder than any verbal reassurances.

Don't Leave A Message

When in doubt, hang up. If they are not available, don't leave a message initially. If someone else answers the phone, just say that you'll call back later. When you try again, if they still do not answer, leave a short message letting them know who you are and why you are calling using the tips outlined in this article. Use an upbeat tone and let them know you look forward to hearing from them. Let them know they can text you back if they are busy to allow them to feel comfortable doing so.

In Closing

Dating can feel like a stressful and high-pressure job interview, so do things that you know help you relax before and after you ask someone out. Try to focus on having fun rather than putting pressure on yourself to find your soulmate. While that may be your ultimate goal, you can enjoy time with people no matter if they are the one or not. At the very least, you can do activities you enjoy and be exposed to new things.

Also see our related guides: Romance Dating ScamsSex & Communication For Partners

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