A middle-aged friend of mine, Cynthia, recently got divorced after 24 years of marriage.

Like many of us, she met her husband in grad school, where the unbridled optimism of youth coupled with dating opportunities that are ripe and abundant make you feel invincible. Back then, you had so many options. Honestly, when I look back on my youth, my single largest regret is dating the same guy all through college. What was I thinking? They said youth is wasted on the young, but truly, did I ever think then that I’d be single this long and relegated to the chicanery of online dating in middle age?

I know Cynthia did not.

I mean, little did I know that as age advanced, the pressures of climbing the corporate ladder, having somewhat of a social life, and finding a mate would be pretty much unattainable. What I learned in my 30s, arguably the most exciting and exhausting decade of my life, is that it’s just really hard to have it all. Cynthia, however, did.

She had a devoted husband, a broad social and professional network, a charming house in an affluent neighborhood, and an accomplished career in the pharmaceutical industry. At some point though, this just wasn’t enough for her. Her career became unfulfilling; she desired to serve a greater cause with a mission. Her husband was committed to Sunday football games and right-wing politics, and as she approached mid-life, she decided to change courses and enroll in law school. And as you can imagine, law school and the subsequent second career she developed as a lawyer, significantly changed her. She began craving more, seeking to spend time with someone with whom she shared common interests. She eventually sought greener pastures, moving to New York City and taking a job with a prominent law firm, offering her partnership and a well-groomed book of business. After settling into her new apartment and adjusting to the billable hours, Cynthia decided it was time to start searching for love again – hence her foray into online dating. I, a seasoned veteran of Tinder, Bumble, and Match, who spent about five years dating online before meeting my prince, tried to give her some advice about how these guys operate. But she plunged in headfirst with little trepidation. In essence, she approached dating like she did lawyering – with zeal, confidence, and allegedly an analytical mind.

Like me, she was very unfamiliar with the all-too-common online dating practices such as "ghosting," “love bombing,” and “benching.” Having dated in the era when cell phones were absent, she simply took men at their word. Back then, men didn’t just say anything, and they certainly weren’t writing or texting it because those means just didn’t exist. I have learned the hard way that men will say just about anything online because a written text, albeit easily saved into perpetuity, doesn’t have the same type of accountability as the spoken word does. And so, the “love bombing” starts with the infusion of constant and consistent compliments – the likes of which can be addicting, especially for us hopeless romantic types. Unfortunately, Cynthia became victim to these shenanigans after meeting a very successful, handsome CEO who literally texted her off her feet. (“You’re so beautiful! I can’t wait to see you again! I can’t stop thinking about you!”) I warned her about this intense type of behavior, but we know well how intoxicating it can be in the beginning. After two wonderful dates, they decided to jump off the dating app, become exclusive, and begin texting and emailing all day like teenagers. Admittedly, she was starting to really fall for this guy. I wish this story had a happy ending that I could share with you. But, after drawing my friend in, he started the oh-so-predictable concomitant behavior of ghosting. When he did reappear, he let her know (via text) that he had been contacted by his ex and had decided to get back together with her. Obviously, this came as a total shock to Cynthia, leaving her confused and heartbroken. She swore to never give her heart away that easily again. And guess what? She shouldn’t.

The advice I would give her or any of my friends is to date with detachment. Date like you’re a lawyer. Look at the evidence. Do not rely on unchecked facts or hearsay. Pay attention to the loopholes in the case presented to you. People can be anyone or anything they want online, and they often do. In order to succeed in this modern game, you just have to stay detached and rational. We often go online as a last resort to loneliness, looking for our soul mate to fill our future days so they are laden with security rather than anxiety. How about dating for the present? Try to get to know someone, take a long walk in the park, or have an interesting conversation over a boozy brunch. I know this sounds like I’m a yoga instructor, but try to stay in the moment and really get to know someone. It took me years to really get to know my soul mate, and while it wasn’t easy to stay out of the sack, in the end, it was worth taking the time to really get to know someone and to make sure he or she is the right fit for you.