I’m Ready to Start Dating. Now What?
I went on dates with 22 men within 13 months between relationships. People get exhausted, just hearing that statistic.
While meeting people to date is often simple, it’s not necessarily easy — I don’t want to minimize the time and energy it takes. It’s easier said than done to stay positive but authentic when dating.
Take a breather. This post is a reminder that:
- Intentionality is key in everything you do.
- You’re not alone in your frustrations with dating.
- Self-love comes down to what you want out of life.
- You know your history better than anyone else.
1 Keep your own needs in mind first and foremost.
Finding what you’re looking for — especially if it’s a lifetime relationship — may or may not happen as fast as you’d like it to. Like me, you might go on dates with 22 people before settling down with someone you really fancy.
As such, it may be helpful to have a game plan for dating yourself:
- What are your needs, wants, and desires?
- How can you fulfill them with or without a partner?
- What other people and resources can you reach out to?
- How can you give that attention to yourself?
It’s not pessimism; it’s having your own back and taking steps to make yourself happy, no matter what happens.
2 Check your assumptions and calibrate your beliefs.
Everyone has a different set of experiences that shape their views on how dating “should” be — what’s expected in a relationship, or what it means to be in one at all!
Where we often get in trouble is when we assume others think the same way we do. The more you can clarify your expectations, the better-equipped you are to express your perspective and see your date’s or partner’s view.
If you still aren’t seeing eye-to-eye about your yellow, red, and orange flags, it’s bye-bye.
Consider the following potential causes of misunderstanding:
- How open are you to being friends with a date? What’s your date’s stance on friendships with people of other genders?
- If it’s exclusivity you’re looking for, what does that mean to you?
- How do you define “friends with benefits”? That could be anywhere from a several-night stand to a full-on friendship without a monogamy escalator.
3 Remember that everyone has an exciting story to tell.
Some dates are just awful, but most people have stories that you can learn from.
What trials and tribulations have they been through in their life? What childhood memories make them smile? What are they proud of? What do they wish they could tell their younger self?
Sample unfamiliar facets of the human condition with them and expand your perspective, even if there’s no escalation after the date.
4 Keep it a sustainable system — whatever that means to you.
If dating is exhausting, it’s okay to take breaks or rethink your dating strategy.
Some do better when making quick, gut-based decisions about whether they see a future with someone after the first or second date. Others prefer to keep the connection low-stakes at first so that they:
- Give their date a chance to become attractive.
- Don’t hype up or project on their dates too much.
The healthiest thing to do is often strike a balance between, “I’m striving for what I want in the long run” and “It’s going to be whatever it’s going to be.” Do what works authentically for you.
5 Have a support team — or at least a few wing-partners
On the flip side, self-love doesn’t mean that you have to exist in isolation or do everything 100% alone. Friends who offer alternative perspectives and keep our blind spots (refer back to point #1) in check make life a lot easier!
That applies both when we’re stuck in our beliefs, and the other end of the spectrum: wavering and needing a reminder of what’s important to us.
6 Remember that the right person for you will offer plenty of flexibility.
If you’re cringing at a first date or an apparent “mistake” or moment of disconnect, that’s okay. It’s part of being human. It’s good to have some self-reflection and motivation to do better, as you know better.
However, if you’re the kind of person to self-flagellate under a microscope, take a step back and see the bigger picture. Intentional dating isn’t about persuading people to like you or altering every little thing about yourself.
Learn about yourself and the other person. Find out whether you’re a good fit. If two people aren’t right for each other, then not being together is the right outcome. It’s not necessarily about what you did wrong.
You can’t “make” people love you, but the right person for you, right now, will appreciate your quirks and what makes you, you. Stay authentic and true to yourself.
7 Reflect on what you’ve learned.
A spreadsheet or quick bullet journal of your dates can be a treasure trove of insight. Keep track of:
- What went well
- What didn’t go well
- What you learned about compatibility
- What you would do differently
I found that spreadsheeting my dates helped me:
- Give myself credit for the things I did right
- Appreciate the work I already have done
- Re-affirm that there are plenty of good people out there
- Recognize old patterns, both good and bad
- Turns out, my patterns weren’t what I thought they were!
8 Above all, trust yourself!
You know your needs, wants, desires, and history better than anyone else. Before you take advice from someone on the internet who’s never met you, consider their biases and where they’re coming from.
(I’m aware of the irony, but here’s the thing: I don’t push a one-size-fits-all solution to everything. I’m only providing the perspective of one person who’s been there and done that.)
If you enjoyed this content, consider leaving a tip!
- Super Smash Cache Ko-Fi page
- Venmo payment to @supersmashcache
As well, when you buy sex toys via my links, I receive a commission at no extra cost to you. Thank you!
- Ava Sol
- Alexandra Lammerink
- Estée Janssens