Newsflash: Being in a relationship isn’t everyone’s main priority. Singledom can be an active choice. Assigning labels like “unwanted,” “unhappy,” or “unfulfilled” to the 51% of Americans between the ages of 18 and 34 who aren’t in a romantic relationship is a totally outdated way of thinking. Now that we’ve cleared that up, what do you do if you’re falling hard for someone who prides themselves on their single status? Dating a person who has been happily flying solo for multiple months, or even years, brings its own set of challenges — and rewards.
Here’s how to handle it.
1. Don’t assume anything.
First of all, don’t decide that your crush has remained single because there’s something off or wrong with them. Being single doesn’t have the same stigma it once did. Relationship therapist Aimee Hartstein, LCSW, explains, “It used to be that you were considered a failure or weird if you were single past a certain age. People are marrying later and there’s much more room for all kinds of alternative relationships than ever before. Being in a committed heterosexual relationship is just one path that people can take, but young people today are designing their own lives.”
Don’t confuse a long-time single person with someone with too many issues for romance. A quick peek at any couple should serve as a swift reminder that being in a relationship doesn’t make anyone perfect.
2. Don’t ask them why they’re still single.
At least, not on the first date — and definitely not in the first five minutes. Even the most well-intentioned questions about someone’s dating history can come off as aggressive, which puts your date on the defensive, since there’s still a slight stigma on singles — especially women.
Jenny Taitz, Psy.D., clinical psychologist and author of “How to be Single and Happy,” puts it simply. “A lot of my clients describe routinely being asked why they are still single on dates and by coworkers,” she says. “So many people internalize this societal stigma, thinking they are somehow not enough without a plus one.”
Even questions that are meant as compliments, like, “How can someone so pretty have been single for so long?” are vaguely insulting. The subtext is that since they haven’t coupled off, there’s something wrong beneath the surface. And the other implication is that singlehood isn’t their choice. Of course, once you know someone better, having an open conversation about their dating history is totally fine. Just remember, single doesn’t equal bad.
3. Do give them their space.
Someone who has been single for a long time is probably pretty used to operating independently and having lots of privacy and down time. Don’t be surprised if they don’t check in as often as you might like, or if they prefer to spend Friday nights with friends or recuperating at home alone over having a date night.
“As a single person you get to do what you want, when you want it,” says Justine Mfulama, a dating and relationship coach in Atlanta, who knows this from personal experience, as she took a substantial break from dating.
Renée Suzanne, a love coach in the Chicago area, also remembers the good things from taking a dating break. “I was afraid [dating would cause me to lose] lose my single-girl life with the martinis, dates, a city apartment, and doing whatever I wanted all the time,” she says. Giving up all that freedom and having to compromise can be difficult for some who isn’t accustomed. Hovering or insisting on more couple time may just backfire. Instead, let your love interest have alone time when they need it. Take a page from their single guide, and focus on yourself.
4. Don’t force labels…or a relationship.
While you may be ready to DTR after a few months (or even weeks) of dating, a person who has been single for a while may need more time. Hartstein’s advice? “Always remember that it takes two people to define the relationship. No one has to just go along with what someone else wants.”
If the person you’re dating isn’t ready to take the relationship to the next level and you can wait it out, great. If not, Francesca Hogi, a bicoastal love and life coach with a dating podcast, recommends being upfront and transparent about your wants and needs. “I see a lot of people who fear giving up their independence and fear having to change their lifestyle. [In this case], make sure you’re clear about what you want. [Dating without committing might be] great for them, but it won’t be for you if you’re hoping they’ll change their mind,” she says.
5. Don’t assume every single person is the same.
Is there a definitive difference between daters who have been single for a few months versus five years? Hogi doesn’t think so. “Everyone goes at their own pace in terms of readiness for a relationship,” she says. “There’s no one-size-fits-all rule.”
And how about dating someone who has never been in a romantic relationship? “The potential rewards are dating someone who has chosen to be in a relationship not out of habit, but because they’re genuinely ready to be with you.” We second that.