How to Know If You Should Keep Dating Someone

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Relationship coach Marlena Tillhon explains how to determine if it’s time to end your relationship
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Dating someone new can be exciting, but what do you do when you’re feeling unsure about the connection? Don’t worry—uncertainty is totally normal, and we’re here to help you navigate it. We partnered with dating and relationship coaches to compile a list of questions to ask yourself when deciding if the person you’re seeing is right for you. If you answer “yes” to most or all of them, it’s a good sign that you’re in a healthy, loving relationship that’s headed in the right direction.

How to Know if You Should Continue Dating Someone

Relationship coach Marlena Tillhon says to look for green flags, like honesty, empathy, and communication skills. Ask yourself if this person meets your needs and shares your values and interests. If they show red flags like disrespect, or you don’t enjoy spending time with them, it may be time to end the relationship.

1

Are they kind and respectful?

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  1. Someone who treats you with respect is someone worth your time.
    Tillhon says, “We need to be with someone who's respectful of other people, of themselves, and of us to build the trust needed to relax into the relationship.”[1] Do they support you and lift you up? Are they patient with you and with others? If they are, give the connection a chance!
    • End things if: The person you’re dating is unkind or disrespectful. If they make you feel small or degraded, or intentionally make you feel bad about yourself, it’s time to move on.

    Meet the wikiHow Experts

    Marlena Tillhon is a psychotherapist and relationship coach based in the UK, with over 12 years of experience.

    Shana Tibi is a certified professional matchmaker as well as a dating and relationship coach.

    John Keegan is a dating coach with over 15 years of professional experience helping people find love.

    Lauren Sanders is a professional matchmaker and dating coach with over four years of experience.

    Emyli Lovz is a dating and relationship coach for men with 14 years of experience.

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2

Do your values align?

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  1. Shared core beliefs and values are a positive sign.
    Dating and relationship coach Shana Tibi says, “Talk about your core values, which have to do with lifestyle, how you manage money, how you see yourself having children, and religion, and see if those core values are the same.”[2] If you have the same core personal values, that indicates strong compatibility. Having shared values is more likely to create a lasting connection.[3]
    • End things if: They have mismatched values that are a dealbreaker for you. Some disagreements are fine, but if you have closely held values and beliefs that they don’t agree with, it’s worth reevaluating the connection.
      • For example, whether or not you want children in the future can be a dealbreaker for couples, even if having kids isn’t on the table right now.
3

Are you on the same page about commitment?

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  1. It’s important to make sure you want the same things out of the relationship.
    This doesn’t always mean long-term commitment and will look different for everyone. For instance, if you want a short fling and they’re on the same page, it’s a good sign to keep dating.[4]
    • End things if: You can’t agree about what your relationship should be. Dating coach John Keegan says, “If you want to be in a committed relationship, and you're with someone who is not being clear or being wishy-washy, you have to make a decision [about the kind of relationship you want] and let that person know.”[5]
    • How long should it take to know how you feel? Sometimes it takes a while to tell if there’s potential for something long-term, and that’s okay! You might take a few dates or even a few months before you know for sure what level of commitment you want. Just make sure you’re communicating openly with the person you’re dating while you figure it out.
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4

Are you equally invested in the relationship?

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  1. It’s a positive sign if you’re both willing and able to invest your time.
    This tells you that your connection fits into your life and that you both feel like it’s worth your time. If you and the person you’re dating both feel compelled to make time to nurture your connection, it’s a sign you can make the relationship work.[6]
    • End things if: One or both of you are unable or unwilling to invest the appropriate amount of time in the connection. The “appropriate” amount of time will vary depending on the nature of your relationship. But if you want more time from them, communicate it! If they can’t or won’t make more time, it’s time to walk away.
5

Do you have shared interests?

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  1. Shared interests can indicate compatibility. Plus, this gives you easy things to connect and talk about, making the connection more seamless. Matchmaker and dating coach Lauren Sanders says you can tell you’re compatible with someone if you have “common interests, values, and life goals.”[7] You don’t have to have everything in common, but a foundation of some significant shared hobbies or passions can be an indicator that you’re a good match.
    • End things if: You have no common ground. Again, you don’t need to have every single thing in common, but if you have no shared interests to bond over, it can be a bit of a nonstarter. If you don’t like any of the same things and are total opposites, you might not be the best match.
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6

Are you socially compatible?

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  1. Social compatibility shows an alignment of lifestyles.
    Do your friend groups mesh well? Do you both like engaging in the same social activities? Love coach Kate Dreyfus says it’s good to ask yourself if you’re including each other in activities with friends and family. These are indicators that it’s a connection worth pursuing.[8]
    • End things if: There’s a major mismatch in terms of social lives. If you’re an introvert but the person you’re dating loves to go out every weekend and only spends time with people who do the same, it indicates social incompatibility. This doesn’t always have to be a dealbreaker, but if you can’t find a compromise, it might be time to end things.
7

Are your communication styles compatible?

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  1. Similar styles of communication make dating easier. Tillhon notes that a good sign when it comes to communication is “being interested in solving problems together and identifying problems instead of making each other the problem.”[9] If you and the person you’re dating have a similar approach to communicating, it creates a solid foundation for a healthy dynamic.
    • End things if: You are consistently unable to communicate well. Effective communication requires active and intentional effort regardless of how well your communication styles align. However, if you find that effective communication isn’t possible even with active effort, it’s probably time to move on.
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8

Do you enjoy spending time together?

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  1. The fun factor is important for a sustainable connection.
    If you and the person you’re dating are always making each other laugh and cracking jokes, that’s a great sign to keep dating. Being able to have fun with the person you’re dating means they make you feel comfortable. Plus, dating and relationship coach Emyli Lovz notes that a shared sense of humor is a good indicator of compatible personality types.[10]
    • End things if: Spending time together feels awkward, forced, or unpleasant. At the end of the day, you should enjoy being with the person you’re dating the way you would with a friend. If spending time with them isn’t fun or enjoyable the way it is with other people in your life, it’s probably time to consider if the relationship is working.
9

Do you feel happy when you see them?

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  1. Your reaction when you see them can reveal your subconscious feelings.
    Dreyfus says to check in with yourself about how the person you’re dating makes you feel.[11] If you have a positive response when you see them or hear from them, that’s a sign to keep dating them. While there are plenty of hard and fast reference points for whether you should continue dating someone, sometimes a positive gut feeling can tell you everything you need to know.
    • End things if: You don’t feel happy or excited to interact with them. If seeing them feels like a chore, it’s probably time to call it quits. Do you want to see them at the end of a long day, or would you rather spend your time elsewhere? Sometimes it’s best to trust your gut and call things off if you’re just not feeling it.
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10

Do you feel comfortable with them?

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  1. Feeling at ease around each other is a huge green flag.
    If you feel calm and safe with this person, it is a sign that you have a secure connection. Lovz recommends asking yourself, “Do I feel at peace? Do I feel safe? Do I feel like myself?”[12] Someone who makes you feel comfortable and relaxed around them is probably a good match.[13]
    • End things if: You feel unable to relax around them. Early relationship jitters are normal, but if you consistently feel tense or on edge when you’re with them, it might be time to find a connection that makes you feel more at peace.
11

Is it easy to talk to each other?

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  1. If the conversation flows smoothly, it means you two click.
    Do the hours just melt away when you talk to one another? Would you two be perfectly content staying up late and chatting without feeling the need to check your phones over and over? Lovz says that if things feel effortless, like you’ve known each other forever, it’s a great sign of compatibility.[14]
    • End things if: You find conversations difficult when they shouldn’t be. Sometimes intimate or serious conversations are hard to have, and that’s okay. But if you’re struggling to drum up things to talk about on a regular basis, or you find yourself sitting in awkward silences more often than not, it might be time to end things.
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12

Can you speak freely around them?

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  1. If you feel comfortable communicating, it’s a positive sign.
    This can mean that you feel safe sharing your concerns or voicing disagreements, or it can just mean feeling comfortable saying things you might hold back around other people. Tibi lists compassionate communication as the foundation for every successful relationship.[15] If you feel secure enough to communicate freely without receiving judgment or a negative response, it’s an indicator to keep dating.[16]
    • End things if: You feel unable to speak your mind or share your feelings and concerns. Someone who shuts you down or makes you feel like you have to walk on eggshells isn’t someone worth your time and energy.
13

Do you trust each other?

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  1. If there’s a foundation of trust, it’s a sign your connection is strong.
    Building trust creates a foundation of security and a feeling of mutual respect. Tillhon says, “We want to look for someone who's open and honest about what's going on in life, sharing details, and not being secretive, so you can get to know them better and trust that there's nothing for you to worry about.”[17] If it feels like you trust one another, that’s a huge indicator that things are going well.
    • End things if: The person you’re dating is excessively jealous. If you feel like you can’t go out or see friends without being questioned, the connection is likely unstable. Likewise, if you feel like you can’t trust them or they’re exhibiting suspicious behaviors, it may be time to reconsider your connection.
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14

Do you celebrate each other’s wins?

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  1. Celebrating each other’s success means there’s a foundation of support.
    Dreyfus says it’s important to ask yourself how the person you’re dating supports you.[18] Being happy for one another when something big happens could mean you’re well on your way to having a steady and mature connection. If they are genuinely excited when things go well for you (and vice versa), that’s a sign that you two are a strong match.[19]
    • End things if: They are jealous or overly competitive when it comes to success. You shouldn’t feel the need to hide your wins or dim your excitement when something big happens. If the person you’re dating makes you feel like you can’t celebrate personal milestones, it might be time to find someone who’s more supportive.
15

Are you both putting in the work?

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  1. Equal effort demonstrates equal investment in the connection.
    Romantic connections require work, so it’s a green flag if you feel like that work is equally distributed. If the person you’re dating is matching your effort level when it comes to making plans, communicating, and problem-solving, that’s a great sign.[20]
    • End things if: You feel like you’re doing all of the work. Sometimes one person has to pick up a little slack at certain times, and that’s fine. But if it feels like a constant battle to get the person you’re dating to give you the energy, effort, and attention you need, it may be time to walk away.
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16

Are they meeting your needs?

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  1. If they meet your emotional and physical needs, it’s a sign to keep dating.
    It’s important that the person you’re dating is checking any major boxes you might have. This will look different for everyone, but some potential needs could be good listening skills, honesty, or respecting your autonomy.[21]
    • End things if: There’s a major requirement that they don’t meet and are unable to compromise on. For example, if your love language is physical touch and they’re not physically affectionate, they might not be able to meet your needs. Lovz mentions that it’s important to recognize if you’re not getting what you need from the person you’re dating and be able to let them go.[22]
17

Is your life better with them in it?

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  1. If you feel like they’re adding value to your life, it’s a sign to keep them around.
    Dreyfus says to ask yourself, “Are you learning something new by having them in your life? Do they challenge you in a good way that supports your growth?”[23] These are indicators that this person has a positive impact on your life. [24]
    • End things if: The connection is doing more harm than good. The person you’re dating shouldn’t feel like a drain on your energy, and they shouldn’t be having an overtly negative impact on your life. Someone who makes you feel constantly anxious or insecure isn’t making your life better.
    • Reader Poll: We asked 375 wikiHow readers if feeling more confident and happy around the person you're dating is a good sign, and 93% said yes! [Take Poll] According to our readers, a partner who makes you feel empowered is an amazing person to have in your life.
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18

Is there potential for a serious relationship?

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  1. Seeing potential for a serious relationship is a good sign.
    This doesn’t necessarily mean you have to know if they’re “the one” right away. But if you can see yourself being in a committed, long-term relationship with this person, it’s an indicator to continue dating them.[25]
    • End things if: You’re looking for a serious relationship and you can’t see yourself being in one with them. If your goal is commitment, but you don’t want to commit to them, it’s time to cut things short. There’s no shame in walking away so you can find a connection you feel more confident about.

How Do You Know If You Should Keep Dating Someone?


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Expert Q&A

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  • Question
    How do you tell someone you don't want to continue dating?
    Lauren Sanders
    Lauren Sanders
    Matchmaker & Dating Coach
    Lauren Sanders is a Professional Matchmaker, Dating Coach, and the Founder of Dating for the Soul. With over four years of experience, she specializes in helping singles find love. Lauren is also the author of Lipstick Faith: A Collection of Inspirational Writings and Life Lessons, You Deserve the World, Rainbows and Strawberries: 100 Devotions for the Brighter Side of Life, and Let's Go Outside Mommy. Lauren holds BS from Dillard University and a Masters from The University of North Georgia.
    Lauren Sanders
    Lauren Sanders
    Matchmaker & Dating Coach
    Expert Answer
    Be completely open and honest about your feelings. Ensure the individual has your full attention and is not distracted so they will be able to fully receive your message. Do not break up over text or phone — it is more appropriate to end a relationship in person if at all possible
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References

  1. ↑ Marlena Tillhon. Relationship Coach. Expert Interview
  2. ↑ Shana Tibi. Dating and Relationship Coach. Expert Interview
  3. ↑ https://www.helpguide.org/articles/relationships-communication/tips-for-finding-lasting-love.htm
  4. ↑ https://www.psychologytoday.com/intl/blog/rediscovering-love/201602/10-questions-help-you-tell-if-youre-ready-commit
  5. ↑ John Keegan. Dating Coach. Expert Interview
  6. ↑ https://www.psychologytoday.com/intl/blog/a-funny-bone-to-pick/202303/you-cant-overlook-this-common-relationship-problem
  7. ↑ Lauren Sanders. Matchmaker & Dating Coach. Expert Interview
  8. ↑ Kate Dreyfus. Love Coach. Expert Interview
  9. ↑ Marlena Tillhon. Relationship Coach. Expert Interview
  1. ↑ Emyli Lovz. Dating and Relationship Coach. Expert Interview
  2. ↑ Kate Dreyfus. Love Coach. Expert Interview
  3. ↑ Emyli Lovz. Dating and Relationship Coach. Expert Interview
  4. ↑ https://www.helpguide.org/articles/relationships-communication/setting-healthy-boundaries-in-relationships.htm
  5. ↑ Emyli Lovz. Dating and Relationship Coach. Expert Interview
  6. ↑ Shana Tibi. Dating and Relationship Coach. Expert Interview
  7. ↑ https://psychcentral.com/blog/how-do-you-create-emotional-safety-in-your-relationships
  8. ↑ Marlena Tillhon. Relationship Coach. Expert Interview
  9. ↑ Kate Dreyfus. Love Coach. Expert Interview
  10. ↑ https://www.psychologytoday.com/us/blog/love-and-sex-in-the-digital-age/201601/12-crucial-questions-about-your-relationships-future
  11. ↑ https://www.psychologytoday.com/us/blog/addiction-and-recovery/202007/are-you-in-a-relationship-with-no-give-and-take
  12. ↑ https://time.com/5373451/break-up-someone-love/
  13. ↑ Emyli Lovz. Dating and Relationship Coach. Expert Interview
  14. ↑ Kate Dreyfus. Love Coach. Expert Interview
  15. ↑ https://www.helpguide.org/articles/relationships-communication/tips-for-finding-lasting-love.htm
  16. ↑ https://time.com/5373451/break-up-someone-love/

About This Article

Marlena Tillhon
Co-authored by:
Marlena Tillhon
Relationship Coach
This article was co-authored by Marlena Tillhon and by wikiHow staff writer, Samantha Fulton, BA. Marlena Tillhon is a psychotherapist and relationship coach based in the UK. With over 12 years of experience, Marlena specializes in relationships, trauma, and anxiety. Through her business, Therapy That Works, she supports clients worldwide in creating secure relationships where they feel loved and valued. She has worked with nearly 800 clients to help them work through inner healing and create relationships and a life that works for them. She is also known online as @lovewithclarity, sharing her professional insights with a community of over 44k followers. Marlena has an MSc in Integrative Counselling and Psychotherapy from the University of Derby. This article has been viewed 139,150 times.
24 votes - 85%
Co-authors: 4
Updated: April 3, 2026
Views: 139,150
Categories: Relationship Issues
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