Dating is a skill that everyone can learn and the reality is that dating in 2025 is not as intuitive as we often think it is or will be for us. Throw in being “off the market” for years, even decades, and that makes dating even tougher water to tread. If you take one thing from this blog, take this: the mindset and energy that we each bring to dating is one of the most important make or break elements to dating. Also, please remember that you deserve to be treated well, while dating and absolutely in your relationships. Yes, that was two things to take away. The truth is that far too many of us accept treatment early on that is way below baseline of what we deserve. Back to mindset: people pick up on the energy that we put down, on a date, speed dating, when we are out and about, and in writing on a dating app. I hear people regularly share feeling tired of dating apps, for really understandable reasons. The way that the apps are described today can sound like online shopping but without all the helpful ratings, and some of our dates somehow end up feeling like a serious job interview, or even like a therapy session, or like an unintentional trauma bonding experience, or just an awkward blind date, or some combination of all the above.
We live in a more disconnected time than ever, where people are able to connect more easily than ever, yet feel more lonely than ever. There is a rumbling in much of the singles community that something isn’t working quite right for many in the world of dating. You’ve probably seen memes and videos about this and find them funny, sad and validating.
People want to feel seen, accepted and connected, but instead feel invisible, questioned and disconnected.
We message with people on the apps, meet in person for dates and speed dates, sometimes only to be met with a line of questioning that makes us feel like we are being interviewed to be considered as an add-on to someone else’s life, or to hear information shares that feel irrelevant to us and like that person is not being intentional or actively trying to get to know us, we message for days on the apps (and sometimes even weeks) only to have our match unmatch, we create rules of how we want other people to show up for us (without their awareness), sometimes not considering how we will show up for them. Many of us have done some of the above because it has become the way of dating for many today.
Personally and professionally, I regularly hear about hurt, loneliness, disconnection, assumptions, expectations, inflexibility, rigidity and pressure… so much pressure. I often support people in moving through confusion, pain and discouragement around dating. It does not have to be so heavy and hard; it can feel lighter and more fun.
Try Different Strategies to Meet People
Something that I have observed that helps many people enjoy dating more is to diversify how we engage and meet people to date. If you are solely using the apps to look for your person, and throw in working from home, then that can feel incredibly lonely. Spending your day interacting with screens will most likely feel discouraging, isolating, and increase the pressure and frustration that you feel toward dating. When we feel lonely and long for partnership, the dating apps dating plan can feel hopeless, discouraging, intense, pressured, addicting and isolating. This often causes people to have an on again, off again relationship with dating apps. It can be helpful and encouraging to have multiple strategies in your back pocket for dating. Here are some ideas and examples:
- Try different Meetup or other local types of groups and show up to activities that you enjoy regularly (eg. groups for hiking, foodies, singles, bowling, dining, sailing, etc.).
- Pick up a new hobby that is social (or engage in one that you used to love) like pickleball, kickboxing, yoga, or some other activity that gets you around new people regularly.
- Do your research and also ask around, ultimately find all of the local companies that offer speed dating and other types of dating events in your area. Stick with your favorites and go often enough that it’s in your routine. You could meet new friends as well as a future partner.
- Let trusted friends know that you are single and looking, as well as what you are looking for in a partner, they might know of someone, or know someone who knows someone.
- Look into reputable matchmaking companies. Many people are turning to matchmaking these days, and different companies offer a wide variety of services. Some matchmaking companies are better than others, so get recommendations! In case fees seem like they are not doable, some offer the option to add yourself to their free directory and they may reach out from time to time if someone who has hired their company could be a fit for you.
- Interact with people often when you are out and about doing life (engage, smile, make eye contact, converse with strangers). This can help you increase the chances of meeting someone, but it also creates great practice opportunities for connecting warmly with the world around you. That practice can support you in bringing magnetic energy to your dates, a kind of energy that is desirable by many.
- Try one or two different dating apps and check them consistently, but not more than once or twice a day…more on this later.
- Widen your circle bigger than it is right now, professionally, in the community, and put yourself in more places where you can connect with others.
Can Dating Feel Better for Me Than it Does Right Now?
Yes, it can. And while there are strategic things that you can do differently, a mindset shift is massive here. Think of dating as a long-term game, reduce the pressure on each date and dating in general, and instead focus on having a meaningful time, learning something new and getting clearer on what you are looking for in a partner. Take the time needed to genuinely connect and try to know new people and notice how you feel before, during and after each date. Having an official or unofficial date debriefing practice can help increase clarity, and it can be fun to do this with a friend (just be mindful that the two of you are aligned and positive about dating), or journal afterward, even if you only write a few brief notes in your phone to support your process.
It can also be encouraging to remember that many people grow significantly during their dating process (if they want and work to).
For example: increasing their self-esteem, raising their standards, understanding how they actually deserve to be treated, reflecting on their part of relationships that did not work, becoming more comfortable with their dating process, improving their flirting skills, increasing their awareness of what is truly important to them in a partner, practicing and getting more comfortable being open and vulnerable but without oversharing, improving communication skills, getting clear on their non-negotiables in a partner, noticing how they want to feel with someone and honestly getting to know themselves better, and so much more.
Dating Inexperience
I often meet people who are in their 20s through 50s who share that they have limited dating experience for a variety of common reasons, or limited dating experience in the last decade or two due to a long-term relationship or marriage. These factors can make us feel more rusty, anxious and generally uncomfortable dating early on, but the more we practice engaging and dating, the easier and smoother it gets for us. It is normal for it to feel uncomfortable or even a bit weird going on a date with someone after being married or partnered for a decade or two or three. I also meet people who have had many years of negative experiences with boys/girls/men/women and are hesitant to date at all. If you truly cannot imagine getting into, or continuing in the dating scene, but you also are fearful of being alone and worry about never partnering at all, then reaching out to a therapist experienced in supporting people around dating can help a lot.
Mental Health and Dating
At a conference years ago, I heard someone say that “The quality of a relationship is as good as the mental health of both people in it.” That stayed with me. From doing this work, it is clear that our mental health, for better or worse, is at play throughout the dating process too. Improving our mental health can lead to more fulfilling long-term relationships, both romantic and platonic. It is important to break patterns that are not serving us anymore in our relationships with others, and our relationship with ourselves.
Mental health support can lead to us feeling like our own mind is a much more satisfying place to be than it once was, and when we feel that way inside, it does show on the outside too.
If you believe that an ongoing mental health issue may be a factor impacting your dating and relationships, then a therapist can help to dig deeper and process what’s getting in the way while dating. We can learn new ways to address issues that we have internalized for years about ourselves and the world around us, learn coping strategies, and reduce different types of anxiety, depression and pain points when dating. Common things people want support with while dating are: increasing their confidence and self-esteem, strategies for managing and decreasing Social Anxiety, anxiety, and depression, support in understanding insecure attachment patterns at play in dating/date choice, and then implementing more regulated and best versions of ourselves of ourselves in life and dating, unpacking past hurtful relationships clouding our perspectives on dating and the gender that we are attracted to, Relationship OCD (repetitive unpleasant doubts and fears about a relationship, date with compulsive behaviors/thoughts that help to temporarily relieve distress from the obsessive thinking), among others.
Rejection, Real or Perceived
When we get a “no thank you,” or someone pulls back or ghosts, it is a no. No’s may or may not be done well or kindly. One of the most common issues that I see in dating and relationships is continuing to pursue after someone has said no in one form or another, and sometimes multiple times and very clearly. If we keep pursuing a no, it has a tendency to hurt us. If we beg for a yes when it is a no, we are pushing past someone’s boundary and it’s also putting us in a position of being rejected again and again. People can be sensitive to rejection (as well as criticism); rejection sensitivity is a real thing. This sensitivity exists on a continuum from being mildly sensitive to rejection to severe emotional pain from rejection a.k.a. Rejection Sensitive Dysphoria (RSD), which tends to be more common for people with ADHD and/or Autism. Rejection can feel incredibly painful for people, so take gentle care of yourself, lean into self-compassion and self-care, and make space in your life for people who will readily love you. That’s the least that you deserve.
It is in our own best interest to remember that a no means no, the other person has a reason and it is their own. People often question if they should follow up and ask their date what the issue was that caused them to say no, and while their answer could certainly yield some some technical issue that we could improve upon, from my experience much of the time it isn’t a technical mishap that we made, but rather just not feeling a romantic connection, not feeling physically attracted, not having had the type of conversation and feeling the type of way they wanted to on the date. If you’re going to ask someone why they didn’t want to go out with you again, be prepared for an honest and possibly painful response. Only ask if you can graciously handle their truth.
Do Not Let One Bummer Date Defeat You
Sometimes we go on a date and the way it turns out leaves us feeling so discouraged, and then we wonder to ourselves if it will ever happen for us. We doubt that there are any good men or women left out there for us. When a date simply sucks the fact of the matter is that the one date simply sucked for us. Sometimes cognitive distortions (inaccurate thinking patterns) go through our minds heavily and then we start to believe them and it causes a cascade of actions, such as deciding we need a break from dating, we are going to delete the apps, and then we turn inward and feel hopeless about dating again. If your goal is to have a partner in life, and maybe kids, then do not give up. If you’re in a funk, then take a short pause and clear your head. Consider pausing the app(s) for a week occasionally if needed and take time for yourself, working to shift your mindset around dating. Be cautious when you are in this state to not talk with friends or family who have a more negative mindset to dating. Two negatives do not equal a positive here.
Dating Feels Uncomfortable and I Cannot Turn Off the Inner Chatter
Turning off (or at least quieting) your inner chatter is an important skill to learn during dates because it can interfere with the possibility of connection, and really kill the vibe if you’re being critical of yourself…or the other person. Humans can be so harsh and critical, of ourselves and of others, and being on dates can bring out the worst in some of us. We can sit across from someone and absolutely roast them in our heads, but trust, the person sitting across from you is not feeling great on that date either. People feel great on a date with us if we’re paying attention and curious about them, we’re in the moment being mindful and attentive, and what can really help is if we have a true awareness of how it feels to sit with us. Think about how you show up on dates in general. Would you want to go on a date with you? (If your answer is no here, some support is encouraged.)
Below are some of the common types of thinking that interfere with dating. So, next time you are going on a date or speed dating, go into the evening simply hoping to have some nice conversations, learn something new, and plan to just meet people until you find that person who you want to date and take the pressure off an evening or a date.
Do you do any of the following?
- Date from a “checklist/check you off” perspective analyzing the other person across from you real time and writing them off as they talk to you? If you are speed dating, do you interview them in 6 minutes to find out the answers to the questions on your list that could almost be sitting on the table between the two of you? If so, connection and chemistry is hard to form in that kind of high-pressure interview style conversation.
- Have a “one up, one down” thinking process when dating, placing people on a pedestal above you, or yourself above them, based on physical attractiveness, education, age, finances, different socioeconomic or cultural backgrounds, a different level of intellectual or emotional intelligence? When we one up or one down ourselves and others, it hurts the possibility of connection and places us and the person across from us in an uncomfortable position.
- Judge, judge, judge, finding something about them, however small, that you do not like, and then your mind magnifies it to the point that it’s all you can see, and so that connection has closed in your mind because you got the ick, possibly over something incredibly small?
- Act quite guarded and closed off to others, making it hard for you both to see each other and make a meaningful connection?
- Self-analyze and judge yourself critically real time on the date, putting yourself down with negative self-talk and telling yourself that you are not good enough for them, or other inner-bullying chatter and put-downs? Number one, you deserve to have a kind inner voice (it feels great) and number two, it’s harder to feel sexy like that.
- Think and speak unfiltered on your date, not being thoughtful, and saying things that could make someone uncomfortable, words that are abrasive, negative, or speaking negatively of your ex, making derogatory statements, engaging in glass half-empty thinking, or acting judgmental or other unpleasantries?
People do think about how they feel with us and if we do the above things, we are less likely to go on more dates. To this people might say, “but this is the real me. They’re going to have to get used to how I am.” On the one hand it’s a great thing to show others who we fully are, and on the other hand, if we try to date often and rarely or never go on multiple dates (that we would like to), it is important to get support in considering: is how we show up in the world somehow getting in the way of us having the kind of companionship that we long for? If so, how? Get support and ask for feedback from trusted friends, family, a dating coach, or a therapist.
Some Things to Keep in Mind When Dating
- See dating to find your person as a long-term process and work to keep your spirits up so you can bring inviting, hopeful, curious energy when meeting new people. Our energy matters so much when dating. To quote Chelsea Handler from a podcast I recently listened to: “you are responsible for the vibe that you’re bringing.”
- Assess your confidence and self-esteem to ensure that you have done the work to invite someone into your life from a place of knowing how you deserve to be treated and spoken to. The higher our self-esteem, the more we expect respect, kindness and consistency from our partner. Unfortunately, oftentimes, the inverse is also true.
- Work to surround yourself with a community of people who are supportive and positive about your dating, and dating in general, and who are not highly critical of an entire gender.
- Be sure to share about your dating life with friends and people who think highly of you and are supportive of you, knowing that you deserve the best and who do not put you down or minimize your worth, ever. Cheerleading can feel helpful when it’s a longer journey. No one needs negativity on this path.
- Find ways to make dating more fun for you specifically. There are multiple ways to find a potential partner and it’s important to both diversify how you meet people and also to have a game plan that feels fun to you.
- It is helpful to consider your core values and those you would like to share with a partner, as well as your non-negotiables in a partner. If you do not know your core values, there are many online quizzes, values card decks and other ways to discover them.
- Work to better understand how other people experience you, to know how you make other people feel and not just your friends but also different people in your life, and people who are just meeting you. Introspect, ask for feedback, and work with a therapist or dating coach if you struggle to get matches, dates, second dates, or want but have not had a long-term relationship.
- If you are pursuing a long-term relationship, know that for many people, especially women, bringing up sex and sexual things while messaging on the apps, or on a first date, can be offputting
- Mirror the other person’s engagement level to some extent. If someone is sending one message per day, notice that and try to show up within a mutual comfort level. If we send a flurry of text messages before they have yet to respond, or we are sending paragraphs and they are sending a few word response, then there is a mismatch in interest, or communication, or attachment or something else. People can feel overwhelmed and step back from connections that feel either grippy and intense or aloof and distant. Remember that most people on the apps are talking to multiple people, and many people using the apps do not check them more than once or twice a day. Some people get tired of the apps and aren’t as invested in the apps as they are invested in finding someone -they don’t know how great you are yet, you’re still a stranger.
- On a date, people are thinking how they feel with you. You will both naturally be considering if the other person could feel like a fit in your life. What so many people share feels offputting and disconnecting is when their date conducts what feels like an interview that gives a sense of “What will you add to my life?” or “Are you worthy of me?” or “Let me tell you all about me,” without thoughtful attempts at genuine curiosity and connection toward the other person. When a date goes this way, it’s hard for our date to feel good and it can even repel people.
- Do not overshare on the first date or two, pace yourself and share more as you get to know someone and have determined that they are a safe person and that it makes sense to share sensitive information with them. A first date does not need to know all about the ins and outs of our past break up or divorce. The first date is a great place to determine if there is some degree of mutual compatibility and chemistry, and it is tough to have chemistry mid conversation about why our last relationship ended. It is possible, but engaging heavily in certain topics makes it less probable.
- Do not go out with someone again if you are positive you do not want to date them, just because you don’t want to hurt their feelings. If the other person knew it was a pity date, they would not want it either.
The Apps
If you are using the apps, then check them consistently but not more than once or twice a day. Something that comes up commonly is that people are feeling addicted to the apps, or they cannot get themselves to open the apps. When we repeatedly check them and have no new likes, it can leave us feeling kinda low. Humans want to be liked, and we are literally not. If we check the apps once a day, there’s statistically more chance of having a like that we like…but if we check the apps 5-10 times in a day, then we’re repeatedly experiencing more times viewing the apps without new likes. Dating for partnership is a marathon, not a sprint, and also not many sprints. If you are using the apps, do it in a way that is sustainable and will not have you feeling burnt out. Based on my experience in supporting people dating and using the apps, and having used them myself, here are some additional ideas that can be helpful in showing up consistently, authentically and honestly on dating apps:
- Ask people you trust for feedback on your dating profile. Unfortunately dating on the apps is about marketing, and most of us are not marketers. Get feedback to support you in creating an interesting and thoughtful profile that honestly portrays who you are and what you look like.
- And to that end, try to use photos within the last year of yourself. If you don’t have up to date photos, ask a friend or family member, take timed selfies with your phone, or work with a photographer. Be sure that the photos accurately represent you. Both men and women complain that a high percentage of people do not look like their photos or that there are inaccuracies in profiles, which leave them questioning honesty. People also complain a lot about filters, face only photos and people only having group photos where they never know who they would be going on the date with so they just swipe left.
- Be who you are on the apps too. Many people are trying to find their one person, and so being who you are authentically on the apps is important if you are trying to attract someone who will like the real you, and weed out people who would not be a good fit for you.
- Show who you are but with reasonable boundaries, without sharing too much such that it would make you feel uncomfortable if your boss, your neighbor, your client, your kid or their friend’s parent, or someone else somehow happened to see your dating profile.
- Use inviting prompts to show how you are unique that make a person want to engage with your profile, and with you. People get dating fatigue, especially on the apps, and it can be easy for people to get swipe happy, and to the left.
- If you do have a job, share that, in some way, shape or form. It’s okay to be a little vague if needed for privacy purposes, but leaving it blank causes people to assume someone does not have any job at all. This is a common complaint.
- Along those lines, be sure that when you engage with a dating app to create your profile and engage with people, that you are in a mindset that keeps your long-term goal in mind.
- A pessimistic or sarcastic tone in our writing on the apps often doesn’t yield the results that we are working hard to achieve…even if it seems funny to write in the moment. I do get it.
- A dating profile with a list of requirements or writing something asking what the other person can offer to make our life better is very commonly swiped left on. It does not leave someone feeling good, comfortable or curious to learn more about us, it gives self-centeredness, which is a fast swipe to the left for most daters.
- A dating profile that has very little writing so that it’s hard to know who they are or that they care enough to put in the time on their profile is another common complaint, particularly with men’s profiles.
- Try to focus on connecting, being curious and having an interesting conversation about each other that is honest, authentic and ideally somewhat fun. People constantly express being terribly bored chatting with random strangers, and how so many conversations sound the same. It isn’t easy or natural for many of us to engage with random strangers virtually, without having that sense of their vibe that we get IRL.
- Ask thoughtful questions when you message in the apps.
- Text consistently if you are interested, not intensely and not dropping off for days and then popping back on. If you are interested, show it, to the extent that’s appropriate given they are a stranger.
- Pace yourself -intense, frequent and repeated messaging before the other person responds feels overwhelming and grippy to many people (and can be an indicator of insecure attachment).
If you struggle with too much or too little use of the apps (and you do want to keep using them) consider the following:
- If you find that you are spending more than an hour a day in total on the apps and you want to cut back, try pairing something that you do not enjoy with using the apps (eg. only use the apps while riding your stationary bike, or commit to completing some mundane task before using the apps and stick with that, set a timer and only use them for 15-30 minutes per day).
- If you find that you cannot get yourself to open the apps and you would like to encourage yourself to, try pairing using the apps with something that you love, and only do it while using the apps, or do something that you enjoy after using the apps for 15 minutes.
Have Fun
Remember to have plenty of fun in the dating process. Keep your mindset positive, stay curious and go into every interaction without expectations, other than to meet someone new and contribute to having a good conversation. From debriefing dates with people, I cannot emphasize enough how important vibes, energy, mindset, whatever you want to call it, is in this process. Show up, engage, be curious, kind, honest and say what you mean and mean what you say. If you continue to stick with it, you will not be single forever, so make the most that you can of this single time period in your life. Do allow yourself to be bummed when you are, but consistently hold your end goal in mind and find meaningful ways to shake off the disappointments. If you need support because you cannot stop negative thoughts, or negative self-talk (that inner bully that so many of us have), social anxiety, you keep dating the same type of emotionally unavailable partner, or something else is blocking you in the dating process, then please reach out to a licensed therapist who has experience supporting people with dating. It does not have to stay this way, life can get a lot better and you do not have to do it alone.
This blog is meant to offer insight and reflection, not medical or psychological advice. It’s no substitute for working with a licensed professional. The strategies mentioned here are general suggestions and may not resonate with everyone. If something doesn’t work for you, please know that this is simply one perspective, informed by my background, training, and experience. Also, any examples provided are purely hypothetical and do not reflect actual people or situations.
