The Potential in Dating

Dating can be an incredibly rewarding experience.

Wait – what? Yes. Dating can be rewarding if you see it as an opportunity for self-growth and knowledge rather than something you have to do to find love.

If you balk at this idea, you may have a story about singlehood and the dating process that could be causing you suffering. If you have a story like “dating sucks,” “men/women only want one thing (sex, money),” “there are no good men/women out there,” or “I’m too old/fat/poor/desperate,” then practice telling yourself a new story.

Imagine the possibility that dating is an opportunity to:

  • learn about yourself, what you like and don’t like, and what you have to give.

  • to help you see and remove barriers that have prevented you from opening your heart to love and be loved.

  • to learn how to be resilient with rejection and learn to validate yourself.

  • to meet amazing people and do things you would have never done if you just stayed at home.

  • to practice communicating what you feel and what you need and sharing the real you with others.

Along with shifting the story you tell yourself about dating and being single, you will also need to let go of your attachment to a particular outcome when meeting someone, and your expectation of how you think the dating process should go - a Buddhist philosophy put into practice. You may want the date to go a certain way, but you can’t expect or force it. While I do encourage my clients to have a goal or intention for dating, be open to being surprised and curious where a relationship or even just one date could go, even if it’s not the right match, you could have a great time and meet a new friend.

I have found that most complaints about dating are rooted in unmet expectations and the thoughts and feelings that accompany dating. If you can learn to be with your feelings - a life skill, not just for dating - and to let go of expectations, you can begin to enjoy the ride and dance of intimacy. To note: Letting go of expectations is different than clearly communicating boundaries, and each are skills that can be learned and practiced while you’re dating.

The following are some tips and ways to orient yourself as you embark on the dating adventure and being single. This is not a list of rules on how to find “the one”, but some pointers toward getting more out of the experience with a highlight on learning about yourself and relating to others. It comes from my experience facilitating a singles program for many years, and my own experience in dating for decades before choosing to get married.

1)   Accept and feel your feelings, including that of loneliness. Even if you’re comfortable being alone, it’s can still be hard to be in your own skin when you’re missing intimate and physical contact. Accept the fact that you may feel sad, anxious or lonely, especially when facing holidays and attending events and family gatherings without a date, or seeing your friends pair off and start their own families. Your body may ache from loneliness, or you will feel awkward and nervous on a date and overthink how to communicate. You will feel the highs of a new relationship, and the lows of a break-up or unrequited love. It is all ok! That is the journey of life, it is a roller coaster. If you want peace and calm, well, then you chose to be the wrong species. When you feel the disappointment from a date that did not turn out the way you wanted it to, learn what you can and move on; bouncing back from the lows fosters resilience. In terms of loneliness, if you’re able to name the feeling, have a good cry, or feel lonely enough to get yourself surrounded by community, you’ll be better off than avoiding your feelings.

2)      Know and communicate what you want and what you can give. If you are just looking for companionship and not wanting to get into a relationship, be clear about that. If your priority is physical intimacy, be up front. If you want marriage with kids, share that, too. Likewise, if you are not sure what you are looking for, it’s ok to share that too, you may need to develop self-acceptance to claim what you’re looking for or what you don’t want. Similarly, be clear about what you are willing to give. If your priority is your kids, your job, or your hobbies and you want to see someone once a month, be up front about that. Let your date know if you are available and like daily texting, or if you prefer to connect over the phone or in person. So many problems and miscommunications can be avoided if you have this conversation up front.

3)      Know your non-negotiables and red flags. Your non-negotiables are things you will not compromise on in a relationship. A red flag is a warning sign that tells you when someone is exhibiting a problematic behavior, or when you are repeating unhealthy and unproductive patterns. This happens when our “unconscious material/baggage” gets triggered (this is a big topic best addressed with the help of a therapist or coach), but also when we are “falling” in love and are extremely physically attracted to someone. Knowing your boundaries and communicating them comes with practice and experience - how would you know a violation until it’s actually happened, and how do you know how to set a boundary if you have never had to? Similarly, we often do not realize which non-negotiables are important for relationship happiness until we have dating and life experience - it’s common to mistake physical and personality traits for non-negotiables and many opportunities for love and friendship are sadly missed. Therapy, coaching, reading and self-exploration can help if you are stuck in these areas, but dating is the place where you practice and take action.

3)      Include your friends. Ask a handful of people you respect and trust to be your support. Ask them in advance if you can text/call and complain after a date, cry on their shoulder, get a reality check or some feedback if they see red flags you are blind to. Rather than put all our expectations, hurts and anxieties on the new people we are beginning to get to know, it’s helpful to have friends that we can express ourselves to.

4)      Text, Phone Call, Coffee, Date: Use dating apps to get off the app. Make 15-30 minute time limits when you get on the app - simply look through profiles using filters, send messages to the ones you find interesting, and respond to messages. Unless you want to practice having conversation and banter over messaging, I suggest messages being directed toward getting a phone number to have a real conversation (some dating apps may have video and phone chat if you’re hesitant to give out your number). We connect with another person’s emotions more when we can hear a voice. Schedule a coffee or walk for a first “meet and greet” rather than a dinner in order to take the pressure off - and, dating can get expensive! Meet for the first time under an hour. This way you are not stuck with someone you have decided is not a fit, and if you really like your date, then you can build excitement and anticipation for another date.

5)      Be sober on the first 2-3 dates to assess how you FEEL and how your body responds. Not numbing yourself will help you read the information your body is giving you. Your heart, brain and gut will give you signals that will be harder to ignore then if you were drinking. Do you feel emotionally safe with them but not as chemically attracted? Do you feel sorry for the person and guilty and obligated to see them again? Are you turned on by their mind as well as their body? Does something feel off in your gut? Your body knows – trust it!

6)      Get in the Deep End. Deep engagement is more nourishing than a shallow interview. You will feel drained if you keep all your first date conversations to a mere exchange of facts and information. Being on a date that feels like a job interview or a test that either of you can pass or fail is not so fun! Curious conversation is a chance to play with each other and can change your or your date’s life based on the encounter you have. Here are 2 ways to get deeper: to presence yourself in the moment, and ask questions that bring about depth (remember the viral 36 Questions to Fall in Love in 2015). To presence yourself in the moment is to tell the truth about where you are at emotionally, what you are thinking, or just the goofy thing that is crossing your mind! It can feel scary and risky (check to see if you have a lot of rules about what you think is appropriate to share on a date) but rewarding in terms of having a genuine encounter. I made a choice in my 20’s to practice radical honesty – I hurt many a man’s feelings, said some appalling things and was awkward AF, but it also benefitted me to reveal my true thoughts, I learned why empathy mattered, and realized men were way more vulnerable than I had thought (another great life lesson and not what I expected). I also learned to appreciate when men were honest with me no matter how much it hurt. The truth was always more freeing and liberating to share and hear.

7) And last but most certainly not least: Date Yourself. Learn to take yourself out on dates…where would you like to go, what kinds of experiences would you like to give yourself, if you have no plans on a Saturday night, take yourself to a dinner and a movie, get dressed up for yourself. It will give you the opportunity to practice the first tip :). Take yourself on a trip for your birthday if no one is available to join you! Don’t wait to be in a relationship to have the experiences you want in life. Give them to yourself. BEING with yourself (without scrolling through your phone) and being great company for yourself is great practice for life and all your future relationships.

If you have a specific question on dating, singlehood, or relationships that I can humbly share my advice, please send it to me to have the answer be part of my upcoming series “Asking for a Friend”: Advice from a Coach and Therapist).

If you’d like more information on 1:1 coaching, click CONTACT to set up a 20-minute chat to assess whether it’s right for you.

Happy dating!

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Connecting with Your Inner Child