Finding the right balance of what you should and shouldn’t ask a match early on can feel like it requires some Cirque du Soleil level acrobatics. You want to play it cool and let things unfold naturally but, at the same time, you’re trying to find out if there’s any potential here ASAP. Some of what you may want to know involves your match’s history. Like, are they fresh off a breakup? Did it end poorly? These kinds of answers can tell you a lot. Knowing the ways to ask a match about their last relationship without it getting super awkward can help you get the info you need without alienating a potential love match.
The first thing to consider is: Just because you want to know, does that make it your business or even OK to ask? Connell Barrett, Dating Transformation founder and dating coach with The League, tells Elite Daily these kinds of questions about your match’s previous relationship are perfectly appropriate to inquire about. “Just be clear on what you want to find out. Are you looking for red flags? Or are you just trying to get a sense of whether or not this person has committed to a long-term relationship? What you want to avoid is ‘fishing,’ and asking lots of questions. This can make them feel defensive,” he explains. Barrett suggests getting these questions out of the way early on. “Anytime in the first three dates is an appropriate time to ask, because it’s in this early phase when you’re both getting a sense for one another and whether you’re a long-term fit,” he says. While it’s fine to ask, talking to your match about their former relationships still requires tact, so here’s how the experts say to broach the subject.
Ease into the conversation.
As with any personal topic, you want to ease into the conversation when you’re first getting to know someone, says Barrett. “Don’t say, ‘Nice to meet you. How many exes have you had?’” he cautions. Instead, keep the topic light. “You might start by swapping ‘war stories’ about crazy, weird dates you’ve had from online dating. This creates a sense of connection and gets you both talking about the topic of dating. From there, it’s a small step to asking about their more serious-dating past,” Barrett explains.
Come from a place of compassion.
Your interest in your match’s dating history might come as a result of something they said that’s led you to believe they haven’t been back out dating long. If you’re concerned that their split is recent and you could be a rebound, Julie Spira, an online dating expert and author of Love in the Age of Trump: How Politics is Polarizing Relationships, suggests a different tactic for bringing up their past: leading with compassion. “You can approach the issue by mentioning that you’re curious to know what tools they used to heal from their last relationship,” she says. “This way, you’re not playing the comparing game, and are coming from a place of compassion.”
Open up about your recent dating history.
Perhaps the easiest way to broach the subject is to just take the initiative and go first. “Volunteer something specific about your dating past. It can be as simple as, ‘Yeah, I met my last partner here on the app, but that ended six months ago, and I’m ready to try again. What about you? When was your last relationship?’” suggests Barrett. “If you offer something first, your date will be more likely to reciprocate without it feeling awkward.”
If you and your match have started communicating regularly, and you feel like you’ve reached a point where you can be more direct, you can be a little more straightforward about what you’d like to know about them, says Spira. “Start the convo by letting your match know how long you’ve been single, and how you’re ready for a meaningful relationship. This creates a safe and healthy communication and path for them to share the same,” she explains. Still, you want to keep the conversation light, as this isn’t an interrogation. “You don’t need the gory details of cheating, or need to know if the sex was good or bad. You need to see if they’re relationship-ready,” she says. “It’s best to start by sharing that you’re over your most recent relationship, and then ask your date if they left their previous relationship on amicable terms.”
You ultimately have a lot of say over whether or not the conversation gets uncomfortable. If you don’t act like it’s a strange conversation, the person you’re talking to is likely to take cues from you and not feel awkward. However, Barrett reiterates that it’s important to keep things light and not belabor the conversation. “Don’t talk about your exes for more than about 10 minutes,” he advises. “Get your question answered and then move on to more fun, ‘datey’ topics — namely, each other. The more time you talk about your exes, the less time you and your date will have to have a fun, flirty date with one another.“
Also keep the vibe positive and upbeat, he adds. “Being negative about your ex on a date never plays well, even if you have every right to feel that way,” Barrett shares. “If the topic of your exes comes up, leave the negativity at home. Rather, frame it through the lens of growing and learning lessons, even if the lessons were painful.”
Getting to know a new match can be tricky, especially when you get into more sensitive subjects, but that doesn’t mean you should be afraid to ask what you need to know. Keep it light, keep it moving, and, hopefully, you’ll get the information you need to decide if you want to keep talking. At the very least, it’s the first indication you’ll have about how well you two communicate. And if it’s not meant to be, or they won’t give you the answers you need to feel comfortable, that’s OK, too. That just means you’re free to keep swiping until you find a match who’s willing to be as open as you need.
Connell Barrett, Dating Transformation founder and dating coach with The League
Julie Spira, online dating expert and author of Love in the Age of Trump: How Politics is Polarizing Relationships