How to start dating again after a break

A dating break can be a refreshing (and necessary) time for self-reflection and enjoying one's own company. After some time, though, you may find yourself wanting to enjoy someone else's company, too.

Taking a dip back into the cold waters of the dating pool can be intimidating. There's the paralysis of choice — not only for choosing a match on a dating app, for example, but choosing an app itself. And then there's the anxiety and all the uncertainty.

Still, if your goal is to meet a partner or even just a hookup, dating is the way to do it.

Here's how to dive back into the game.

Am I ready to date again?

The first question to ask yourself is whether dating again is right for you at this moment. Only you can answer this question. Know that your pace may be different from that of others, said Kiana Reeves, somatic sex educator and chief content officer at the plant-based sexual wellness brand Foria. As you ponder whether you're ready, focus on what gives you pleasure in terms of self-love, but also make sure to engage in other activities you enjoy, such as spending time with friends and family.

"Enjoy experiencing your life at your preferred speed, and the rest will follow," said Reeves.

Figure out your motivations for wanting to date. If it has to do with "proving a point" to an ex (that you're still desirable, or that your relationship is really over), don't start dating, said Joe Kort, PhD, certified sex therapist and co-director of sexual medicine training provider Modern Sex Therapy Institutes.

The same goes when you're looking for a new relationship to alleviate the pain of your previous one. That doesn't work, said Kort.

"We live in a society that has a fast-food approach to dating," said Reeves, "and moving from one thing to the next is pretty common." As such, you may feel "single stigma." If you want to date because you think being single is somehow wrong, or because you can't stand being alone, that's probably what you need right now — to spend time with yourself, not a new partner.

Kort also dispelled a couple longstanding dating adages as myths. The first is that people have to wait a certain amount of time to assure they're "over" their past relationship before getting back out there. Instead of setting a calendar date to re-download Tinder, Kort advises trusting yourself and how you're feeling.

The second myth is that people shouldn't get into a relationship until they're "healthy" again. If you need time — especially if your past relationship was in any way traumatic or abusive — take all that you need. But if you're itching to get back out there (for reasons other than trying to "prove" something to your ex or something similar), there's no need to set timelines.

In addition to trusting yourself, Reeves said to be honest with yourself and others about where you're at.

Licensed psychologist and relationship expert Nikki Coleman said to ask yourself two questions: Will dating again enhance my life? And, do I want to expend my energy dating right now?

Dating is a numbers game, Coleman said, which means spending time and mental capacity (and oftentimes, money) to find a match. "If you're truly ready to get back out there," she continued, "then the frustration, disappointment, and sometimes even anxiety associated with dating will be a worthwhile endeavor."

The only person who will know if you're ready to date again is you, no matter what well-intentioned family and friends say.

How do you date after a long break? Credit: Bob Al-Greene / Mashable

How do I date after a break?

You've done some self-examination and you've picked out the best photos for Bumble. Now what?

Reentering the dating world can bring up a slew of emotions, Reeves said, including apprehension, excitement, and uncertainty. Beginning with some clarity about what you want can help.

Are you looking for a long-time relationship or a cheeky hookup? Having a goal in mind can help guide you in how you want to connect and how to go about it. For someone seeking a long-term relationship, for example, the "designed to be deleted" Hinge is probably a better app option than sexual exploration-minded Feeld.

Having an intention can help you identify qualities you're looking for in another person as well. Do they seem ready for a relationship, or whatever connection you want?

At the same time, Coleman urges people to stay curious and open to possibilities. Dating should be fun, she said, and an exploration of yourself as much as getting to know someone else.

As such, you can reframe this experience. Instead of focusing on the negative — say, how long it's been since you've dated — you can think about all you've learned about yourself and what you want.

Whether you set a goal or not, start slow, said Coleman and Kort. It's OK if you're rusty. There's no need to, say, schedule five first dates in a week.

You don't want to burn yourself out or set unrealistic expectations for your first few dates. "Building connections doesn't happen overnight," Reeves noted, "even if attraction is instant."

Set boundaries with yourself and others. Coleman suggests making a checklist of all the things you need to feel as safe and secure as possible. Say you only want to go on one date a week, or you don't want to text a potential match all day. These are all reasonable requests — you just have to be honest with your dates about them.

Know that you can put on the breaks anytime if a relationship isn't moving in a direction you like, said Kort. Video or phone dates are also great options if you find that you're not ready for in-person connection.

Above all, remember to enjoy yourself. As Coleman said, "Dating should be fun, or don't do it."

Am I ready to have sex with someone new?

Reeves suggests pacing yourself with sex, as with dating. Embrace the activities that make you feel good, whether solo or with a partner. Ask yourself what intimacy looks like for you. Figure that out before getting intimate with a partner.

Kissing for the first few dates or just hand-holding and talking is more than OK, and can actually forge a deep connection, according to Reeves. "These types of activities build trust and help our nervous systems regulate in the way we need to feel safe in sexual intimacy," she said.

While your body may want sex (signified by getting aroused), your brain may need more time. You can wait until you get a resounding yes from your mind that you feel safe and ready. If you're feeling awkward about sex and intimacy, you're not alone, especially if you're reading this in the midst of the pandemic.

Once you're ready to sleep with someone new, Reeves suggests coming prepared for the best experience. Pack condoms, lube, and whatever else you need to feel most comfortable.

Have an open conversation with your new partner about your boundaries and what feels good for you. You'll end up doing what gives you the most pleasure, and you'll be at ease knowing limits have been set.

Awkwardness around these conversations are par for the course. "Sometimes the questions and communication in this stage can feel awkward," said Reeves, "[and] that's great! It means you are staying curious and open, and it's a good sign that honest communication and learning are happening."

Open communication doesn't just lead to the feeling of safety; it also leads to better sex, period.

Dating after a break can be nerve-wracking, but through honest conversations — with yourself and others — and mindful steps, you may find yourself splashing happily in the deep end.

This article was first published in 2021 and republished in 2024.

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