Lessons from a Matchmaking Pro’s Sponsorship Adventure
For those of you who know me, you might have heard that part of my intro or bio mentions I never used dating apps. While I did navigate the dating scene in America, technology was a whole different ballgame back then, and attitudes towards dating in the South Asian community were completely different! Luckily for me, I have an amazing team of both singles and committed folks who keep me young and relevant by sharing the struggles singles face in today's modern dating landscape. The more I work with clients, the more I realize just how tough it is out there. So, I keep up with the latest through industry groups, articles, podcasts, and pop culture.
Recently, I got a firsthand experience of the dating world's challenges while soliciting sponsors for our upcoming Third Annual Speed Dating Event. If you haven't registered yet, do so ASAP—it’s going to be our most ambitious event yet! We even have an optional Desi Singles Gala afterward if you want to make a day of it!
Our Biz Dev manager has been sending out hundreds of cold emails and DMs to potential sponsors, which feels a lot like blindly swiping on a dating app without too many parameters or filters—just shooting your shot and seeing who responds. One vendor replied, intrigued by our low-cost community partnership option, but had some questions. After a few days of back-and-forth texting, we decided it would be better to chat on the phone. We scheduled the call, only to have it rescheduled twice, and then we got ghosted once. Finally, after conceding that maybe she wasn’t comfortable with a video call, we settled for a regular phone call—and the inquisition began!
The whole back-and-forth, rescheduling, cancellations, and change of format felt eerily familiar—like the getting-to-know-you phase after matching with someone on a dating app or through Single to Shaadi’s matchmaking platform. Often, a connection doesn’t form because of the logistical gymnastics and people treating their time like it’s the crown jewels. They only want to invest energy once they’ve ticked all their boxes or filled out their biodata. And let's not forget the mind games and playing hard-to-get, which can make it feel like we’re chasing them down. If it’s going to be a no, just say no instead of stringing someone along. This way, everyone can move on to find a better fit.
When we finally got on the call with this vendor, there were a million questions—many of which indicated she hadn’t read the email or sponsorship deck we sent her. The repetitive questions made me feel snarky, and I ended up pointing her back to the previous email, which already felt contentious and put me in a bad mood. It almost made me decide I didn’t even want to work with her. But, I put on my big girl pants and followed through with the conversation, which only reinforced my initial feelings.
The questions were so specific and niche that it felt like I was being interviewed on the spot, which made me uncomfortable. My vibe was friendly and energetic, more of a "let’s get to know each other" tone, while she was all business, asking, "What can you do for me? How can you guarantee success?" It’s like dating someone who jumps straight into interview questions: "What’s your timeline? Tell me about your exes. How many kids do you want? Do you have any debt?" You completely skip the chemistry and humor—key components of compatibility. I hate when people go on a first date or Facetime only to ask a laundry list of questions, then say it won’t work out for some trivial reason. Even with our package clients, sometimes I have to remind them to look past the nitty-gritty details in a profile. For example, we once shared a profile of a gentleman who enjoyed biking and hiking. His pictures clearly indicated he had more of a dad bod, which leads me to think his passion for being active isn’t an obsession, yet our client rejected him, assuming he was too into health and fitness, which was not her vibe, without considering other aspects of his profile. Sometimes, having too much information can be paralyzing, causing people to avoid taking a chance unless they see a guaranteed sure thing. One client rejected a guy on Hinge because he didn’t have his dating goals section filled out! (Note to guys: women read EVERY WORD you put on a dating app and read even more into what is missing!)
After all the back-and-forth and answering her questions, she had the nerve to tell me she was going on vacation and wouldn’t be able to make a decision until she returned in two weeks! When I asked if I could follow up with her when she got back, she said she’d follow up with me because she didn’t know how much time she’d need to recover and catch up after vacation. At that point, I wished her a good vacation and moved on. I told our Biz Dev manager this opportunity probably wouldn’t pan out. If someone needs two weeks to make a decision on something so low-stakes, it doesn’t bode well for building a relationship. When our clients tell us they connected with a potential match but their next meeting or connection point isn't going to be for two weeks, I'm equally dumbfounded as to how they can just let somebody linger for two weeks, especially when they are more than likely going to reject them. If you're going on vacation, take this time as an opportunity to invite your new match into your world and see how they react and respect your boundaries, rather than just putting everything on ice and thinking you can pick right back up whenever you have time. Because chances are, that other person has moved on, and now, so am I!
I understand how tough it is out there, friends. While my experience wasn’t from the dating perspective, going through a frustrating “match to meeting” process that didn’t yield results gave me a glimpse of what daters face. I can see how multiple situations like this can lead to jadedness and frustration. So, let me lead by example and jump back into it—sending out more cold emails and continuing the process. My ultimate goal is to make our speed dating event a complete success and a memorable experience for everyone involved—attendees, vendors, and team members alike! So I'm not going to give up and neither should you!
To all you daters out there, get back on those apps and start swiping! But be intentional and know how to show up, so you’re not contributing to why the current modern dating landscape can be so challenging.
