It’s not uncommon for people to include pictures of themselves with their friends in their dating profiles. In fact, there’s a rare contingent that includes their friends in all five of their pictures, leaving you to play a process-of-elimination game where you have to figure out which person is in all five of these photos and owner of the profile you’re viewing.
It’s not uncommon to look at someone’s profile and think the profile owner is attractive enough… but their friend is beautiful! Channeling my inner Seinfeld, I sometimes wondered if it’s possible to figure out who the friend is and pursue her, instead.
And then the opportunity presented itself.
While I was living in Wisconsin, I was looking at a profile on Hinge that continued to present itself. The woman who owned the profile didn’t really stand out to me. But what did stand out was the woman posing with her in one of her profile photos. This woman was a knockout. Probably the most beautiful woman I’d seen in a Wisconsin profile. But it was someone else’s profile, and I didn’t have any information on her.
Around that time, I was talking to my friend Dannica about this profile and wondering aloud how I could figure out who this woman was and try to connect with her without appearing to be a psychopath.
Dannica said, “Send me the profile.” So I took screenshots of the profile and sent it to her. Within minutes, she had found the Facebook page of the woman who owned the profile. While we were talking, she perused all of the photos on her Facebook page until she found a photo that included the woman friend in the Hinge profile
The photo was tagged, so she identified the woman as Tracy and visited her Facebook page. From there, it was easy for Dannica (who is an HR person and no stranger to doing her own background checks on people) to find Tracy on LinkedIn and figure out through records that she was divorced
So not only did we figure out who this beautiful woman was, but that she was also divorced and potentially single. Coincidentally, she was also the head of HR at a company to which I had recently applied. There was actually a reason to contact her!
Growing up on Fred Astaire movies from the 1930s, where romantic pursuits were seen as silly, cute, light-hearted, and fun, I thought this could be an entire plot. We just needed to write some memorable hit songs and present them with some phenomenal dancing.
But how times change. It’s 2025, and what was once an innocent pursuit was now a creepy stalker creating an unsafe environment for some unsuspecting woman. And with sites like “Are we dating the same guy” out there with hyper-paranoid women (and hyper-paranoid men, on the “Are we dating the same girl” sites), the last thing I needed was not even be aware that I’ve now been branded by a story that would probably be about 5% true. (And for those of you who would say, “See, the “Are we dating the same guy” site worked,” wait until the end of the story before you claim your victory.)
The only way I could think of to meet her organically was to make contact on LinkedIn and see if I could procure a deserved interview for the job I was seeking. She did accept my connection request, but then never responded to either the LinkedIn message or email I wrote to her work email.
With that avenue seemingly shut down, I couldn’t think of a way to write to her and explain the situation without risking looking like a creeper. And I didn’t want her to feel vulnerable like that, so I gave it up.
Until I left the state and moved out of Wisconsin…
After I left, I figured it couldn’t hurt to satisfy my curiosity and see if I would’ve had a chance. Hopefully, the worst case scenario would be she took it as a compliment and we all just moved on. So I wrote her this email to her personal email address (which I got from her LinkedIn profile):
“Hi, Tracy.
My name is Jon, and I wanted to share a story with you that I hope you'll take as a compliment.
I'm on Hinge, and a few months ago, I ran across the profile of a friend of yours. (I think her name is Jennifer, but I don't remember, at this point.) I didn't feel much connection to her profile, so I would've passed on it. (Not a cut on your friend... not everyone connects with everyone.)
But her lead picture featured her with another woman who was one of the most beautiful women I've seen on Milwaukee's Hinge. I started talking to my friend Dannica (trying to be transparent), who asked me to send her the profile. She bet me she could figure out who it was.
She quickly found your friend on Facebook, and then quickly found a photo of her with you with your name in it. It was only minutes before she told me your name. She then researched you a bit and told me you were divorced.
Separate from all of this, I had applied for two different roles at your company. So when I looked at your LinkedIn to see you were in HR there, I couldn't believe the connection.
It was great to learn who you are, but this entire story was so illustrative of just how accessible personal information is to anyone who knows how to look that I couldn't figure out a way to write all of this to you without looking absolutely creepy. It was a question I discussed with many friends (male and female): Is it possible to connect without looking creepy? We pretty much all concluded it wasn't. The risk was too great. So I didn't.
I've always wanted to share this story with you, but I didn't want to concern you in any way. I've since moved out of Wisconsin, and so the ability to meet you has passed (as you can see on my LinkedIn). But if nothing else, I wanted to share this story with you simply to tell you, you are pretty stunning, and you seem to be a pretty good person, as well.
I hope all's well with you. And I hope you take this as intended. I don't live there anymore. I'm not stalking. I won't contact you again. But I thought it was an interesting story, so I thought I'd share.
Take care.
Jon”
And I hit “send.” It was out there. I was finally going to get my answer–even if it was no answer at all. But in the same day, I received this response:
“Hi Jon,
That's a pretty great story and I appreciate the very kind intent behind it. If it makes you feel better, you made it not creepy.
Congratulations on your move! I hope that it went well for you.
Dating is tricky these days. I avoid dating apps (and dating).
Sending nothing but good thoughts your way for complete success.
Take care,
Tracy”
She got it! She understood the intent, and responded in kind. Leave it to Wisconsin to keep perspective, see it for what it is, and handle it with kindness and grace.
Though, with all that said, I’ve concluded there’s not really a great way to pursue “the friend in the picture.” But I’m glad I wrote to her and let her know what happened. Sometimes, you just have to satisfy an innocent curiosity.