Should You Look Up Your Lost Love?

“Whenever there’s space for your imagination to play a role, it will,” says Catalina Toma, a media psychologist and communication science professor at the University of Wisconsin-Madison. “It will kind of fill in the blanks with what you want to believe and what’s consistent with your previous experiences.”

What’s more, social media allows people to be bolder than they would be at a reunion or football game — and their advances aren’t always welcome.

Cynthia L. Dorsey, a director and producer who splits her time between Washington, D.C., and New York City, knows this all too well. When a former boyfriend sent her a Facebook friend request and message years after their breakup, she was initially hopeful. The ex had broken her heart by seeing other people behind her back and never acknowledged a soul-baring four-page letter she had written him. But maybe he had matured; maybe he would apologize.

Dorsey remembers thinking, I wonder if this could be something, or we could at least start a friendship. But all too quickly, the ex’s “Hey, beautiful” spiraled into sexual advances. She blocked him.

Geoffrey Miller and Janet Galope at his 2009 high school reunion (left) and in 2025. Galope mostly remembered Miller as a nerdy chess kid back in their Washington, D.C.–area middle school.

Courtesy Janet Galope, 2

A (chess) partner for life

Sometimes it’s not an old flame who reaches out, but someone you barely knew.

This was the case for Janet Galope, who mostly remembered Geoffrey Miller as a nerdy chess kid back in their Washington, D.C.–area middle school. Her crowd was more into hard rock than board games. The two sat next to each other in Mr. Timberlake’s history class but, like typical middle schoolers, they never spoke.

So when, in their 40s, Miller responded to Galope’s Facebook post seeking a chess partner, she took it at face value. She’d never been married and had two kids, including a teen with significant disabilities. “Most people would run from that situation,” Galope says.

But when she and Miller met up, they talked for hours. Days later, when Galope’s son was in the emergency room, Miller met them there. Soon enough, Miller admitted he’d had a crush on her 30 years ago.

“It was like I’d known him forever,” Galope, now 60, says. And in some alternate universe, she had. The duo had been to many of the same concerts and some of the same professional events. (She’s in cybersecurity sales; he recently retired from the government.) They both followed pescatarian diets and wanted a vintage Corvette. “We were just meant to be, because our paths had become so close, and [then] they finally crossed,” says Galope, who has been married to Miller — whom she has yet to beat in chess — for 11 years.

Beauty and The Chief

Esther Rose didn’t need Facebook to suss out what her grad school ex was up to: He was NBA Hall of Famer Robert Parish. Google did the work for her. “There was always that lingering What if?” says Rose, who would occasionally search to see how Parish was doing and whether he had remarried. (He was divorced when they met.)

But one day about nine years ago, Rose wanted the real-life scoop. She had been married, had a child and was getting divorced. She’d never forgotten how down-to-earth Parish was and how special he made her feel when they were dating. “Even during the season, when we were apart, he would send me flowers, CDs, cards,” she says. “I actually still have the cards.”

Newly separated and on business in Dallas, a three-hour drive from Parish’s home in Shreveport, Louisiana, Rose shot her ex a text, asking him to dinner. The famously stoic athlete, who’s nicknamed “The Chief,” replied “yes” without hesitation, she says.

The rest, they say on their TikTok channel, is history. Now Rose, 59 and based in Plano, Texas, and Parish, 72 and still in Shreveport, text and FaceTime often to make their long-distance relationship work. “We have our own lives but also one together,” says Rose, who owns a legal marketing firm. “It’s crazy that we met 31 years ago and are living happily ever after.”

So you want to text your ex

If you’re considering making a digital move on someone from your past, follow these tips.

1. Know your motivations. Be honest with yourself about any current romantic partners and the intended recipient before hitting send.

Oftentimes a preoccupation with old flames prevents single people from being open to new love in real life, says Orbuch, author of Finding Love Again: 6 Simple Steps to a New and Happy Relationship. “Sometimes we haven’t let go of the emotional baggage connected to the person,” she says. “But if we don’t let go of the past, we can’t see that person, or we can’t see new people, for who they really are.” In cases where you can’t shake off those strong emotions, it’s better to limit or cut off social media contact rather than wallow in what was.

Other times, people in relationships are tempted to reach out to an ex because they want a quick hit of admiration or want to make their partner jealous. It almost always backfires. “It’s so important to work on the current struggles with the current partner so that you’re not reaching out for the wrong reasons,” says Orbuch.

2. Manage expectations. Toma calls social media profiles “glamorized glimpses into somebody’s life.” The touched-up selection of postings is curated: a vacation here, a promotion there. No one is advertising their crummy commute or double chin.

That’s why it’s a good idea to move online communication to real life within a few weeks if a potential romantic connection is mutually on the table. “When you meet them face-to-face, that bubble of idealization tends to burst,” Toma says.

And be prepared for your outreach to go unanswered. “If the former flame does not accept a friend request or does not want to engage in communication, that’s totally fine,” says Toma. Respect it and move on.

3. Accept whatever comes. Even if an attempt at reconnection lands you in the friend zone, that can be a net positive. Having a variety of social connections, from your dearest friend to the desk attendant at the YMCA, is important for health and well-being, and for keeping loneliness at bay.“If it doesn’t work out in terms of a romantic relationship, it’s great to have that connection with somebody from the past and continue it into the present,” Orbuch says.

Plus, research suggests that other people tend to like us more than we think they do. People we’ve lost touch with usually appreciate hearing from us; they just don’t want to make the first move. Why not you?

“There are a lot of people out there, and all you really have to do is say hi or ‘What have you been doing?’ ” says Steve Gove. “It’s just an amazing life, really.”