Whether you’re newly divorced and finally feel ready for a partner again or are much newer to the love department, online dating can feel daunting. How do you design a profile that’s both inviting and authentic? And what about those dreaded photos? One thing’s for sure: There is clearly a lot to consider, that’s why we’re bringing in an expert.
New York–based personal stylist and dating coach Alyssa Dineen found love through online dating after a divorce, which she writes about in her book The Art of Online Dating. With clients ranging from their 20s to their 80s—in locations all over the country (thanks, Zoom!)—Dineen guides them as they set up their profiles and even helps them style and arrange professional photo shoots to capture those oh-so-important dating app pictures. Below, we asked Dineen to share her expert advice on this often tricky task. Read on for every detail.
Oprah Daily: Why are many people nervous to start online dating?
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Alyssa Dineen: When I jumped into it, I didn’t know what I was doing, and I didn’t really have anybody to turn to. All my friends were still married. I had a couple of single friends who had been online dating for a long time. To them it was just like: “Oh, you just set up a profile. It’s no big deal.” I think you forget how there’s all these nuances to it!
Coming from a photo and fashion background, it was pretty easy for me to figure out what photos worked. Writing the bio—knowing what to write—took a lot of trial and error. Then you get to the actual part where you have your profile up and it looks great—but then you need to actually message people and make a date.
Figuring all that out and forcing myself to go out with new people and keep an open mind–it became a fun social experiment along the way. I eventually met my partner. We’ve been together for over five years. When I met him and he found out that I was a stylist and an art director, we were talking about how I could kind of help other people who are like us: people who were new to online dating–especially people our age and older, 35 and up. It’s not something that you’ve grown up with, so [it] can be all new territory if you’re coming out of either a long relationship or a marriage. I wrote the book, The Art of Online Dating, as a guidebook to help people like me and like my boyfriend jump ahead of the learning curve and get to the actual dating.
What advice do you have for people who are genuinely nervous to try dating apps?
One important thing to do for people starting from scratch is to ask around. When I was doing it, there was more of a taboo, like you don’t talk about your online dating. And now it’s so different. Just getting to that point where you can ask friends for advice, or ask around to people who maybe are younger than you is the first step.
Once you can get to that, there’s tons of research and things you can read about it. I have courses that help you jump-start getting your profile up and running. A lot of people come to me with resistance, like: “Well, I really don’t wanna online date, but everybody says I have to.” You have to get out of that way of thinking, because it really is beyond that.
This is just what life is now, you know? And sure, you might still meet somebody at the grocery store, and that’s amazing. But everybody’s online dating. If you really are proactively wanting to meet someone, that’s just what you have to do.
Do you have advice for anyone who wants to put themselves back out there after a divorce but feels like the dating landscape has changed since they were last dating?
It’s changed so much. One thing that hit me pretty quickly is: “Oh, so much of dating is actually texting.” It really is so much about practice and getting used to that—messaging with people and deciphering texts.
I think so much of it is experience and putting yourself out there and practicing. It took me so long to even get to the place where I was comfortable messaging back and forth, and not overanalyzing every little thing I wrote.
It took me a while to get to the point where I would actually just start asking people out myself. People in my generation and older, a lot of women don’t feel comfortable with that yet. And that’s something I really push people to do. You’ve got to put yourself out there. You’ve got to be proactive.
It almost sounds like dating apps can be fun!
That’s what I hope I was conveying in my book: You can actually have fun with it! It does seem really daunting at first, but really, you just kind of need to let go of the control of it. And in the process, you get to know yourself, just by virtue of having conversations with new people and talking about your story.
What is the biggest misconception about dating apps?
First of all, that it’s all negative and bad. I think so many people go into it sort of dreading it, as if it’s a last resort. That just makes me feel so sad because it so doesn’t have to be that. And again, I know it’s up and down; it’s not always super fun. But going into it as positively as you can and just knowing that it does actually…people do meet online.
I have clients in their 70s who have met their next partner; in their 60s, in their 50s, in their 40s, in their 30s, in their—really, it can work for any age, which I think is amazing. If you really put yourself out there, keep an open mind, it actually can work.
It’s funny to me when, like, a 55-year-old comes to me and she’s like,“I’m too old. I shouldn’t be…” I’m like, “Are you kidding me? I have an 85-year-old woman who’s out there. You can do this.”
A picture is crucial to your dating app profile. What are your top tips for taking great photos?
People [in] my generation aren’t used to taking photos of themselves. Even doing what I do, I had no photos of just me. It was either my kids, or my husband, or my friends. You didn’t really think to have photos of yourself. I’m really encouraging clients to practice selfies–I talk about that in the book, and I’m talking hundreds of selfies. You’re probably gonna delete the first 500!
You’d be shocked at how many people still just have one photo on their profile. And they think that’s okay. They don’t realize that you need five, or six, or seven, or more, depending on the app. I talk a lot about styling yourself for your photos, and keeping it somewhat simple. And make sure you have clear, waist-up photos, no sunglasses.
What details should our readers add into their dating app profiles?
Staying away from negative talking in your profile is huge because a lot of people do tend to do that—like: “Not looking for any drama.” Just really keeping people positive.
You also have to be unique and stand out. You can’t just write, “I like yoga and going to restaurants and red wine.” You have to think of the most unique things about you. Instead of just “I like travel,” be specific: “I like going to [this] specific place because of this and this.”
Let’s say our reader is getting ready for the first date with someone they met online. What’s your styling secret to help someone feel confident for a first date?
Don’t reinvent the wheel every night you go out on a first date. Just pick an outfit you feel great in and you know you look good in. Walking out the door, you’re gonna feel really confident.
This person has never seen you before. You can literally just wear the same outfit every time. And it’s your go-to, and you know you feel good, your shoes don’t hurt, you’re not fidgeting with your shirt, your pants aren’t too tight…taking that out of the equation is huge, because everyone’s already so nervous on a first date.
This interview has been edited and condensed for clarity.
Jane Burnett is an Assistant Editor at Oprah Daily, where she writes a variety of lifestyle content for the editorial team. She’s a journalist with a pop culture sweet tooth—when she isn’t catching up on celebrity news, she’s usually listening to a podcast! Jane was previously an on-air reporter in local news, and worked at Thrive Global, Ladders News, and Reuters. She also interned at CNBC through the Emma Bowen Foundation, and is a member of the National Association of Black Journalists (NABJ).
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