I Hired an Online Dating Coach and This Is What I Learned

Spoiler alert: It's a lot.

I Hired an Online Dating Coach and This Is What I Learned

Spoiler alert: It's a lot.

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Full confession: I hate online dating. I believe it dilutes the magical process of meeting someone into a sterile affair that makes me feel like I’m an HR rep sifting through endless résumés. It also feeds into the paradox of choice: the seemingly bottomless array of options offered up by online dating makes people less likely to make any decisions at all. And it’s normalized some truly terrible behavior, like ghosting, orbiting and breadcrumbing, turning people into disposable objects. Not to mention, in the era of tech addiction, I hate the idea of spending any more time scrolling through my iPhone than I absolutely have to.

Given that I’m busy and that it’s so popular, I decided to give the world of online dating another go, but this time, with some professional assistance. My previously terrible experience with a dating coach showed me how important it is to get a good one, so I enlisted the help of NYC’s top matchmaker: Sameera Sullivan.

The elite matchmaker, who runs the service Lasting Connections, predominantly works with high-profile clients for a hefty price tag—her services start at $45,000 for a year of in-depth coaching that includes everything from running your dating profile to choosing your wardrobe. But you get what you pay for and her success rate is one to be envied.

She also provides a virtual coaching program (rates start at $6,500 for 3 months), in which her Matchmaking Coach takes over your profile, writing your bio, taking professional shots of you, choosing people for you to message, and providing feedback and guidance on your exchanges.

Not everyone can afford Sameera for individual sessions, but she’s the best, so I recently reached out to her about my own romantic woes, and asked for advice that I could share with other readers struggling in the online dating world. Here’s what I learned. And for more coverage of the crazy world of dating in 2018, don’t miss the 20 Online Dating Terms Older People Don’t Know.

tinder profile photos

1
Choose Natural Photos

You want your photos to paint a picture of who you are and the exciting life that a potential partner could have if they were with you. Looking over my photos, Sameera liked that I had plenty of images that showed that I’m a fun person who travels a lot and likes to have a good time.

The other benefit is that they make it easy for someone to use the photos as a prompt for a non-generic message. They could see my sailboat photo and ask, “Where was that taken?” or look at the photo of my dog and say, “What’s his name?”

She told me to remove the selfie, because selfies provide a distorted version of your face (which is backed up by studies). She also advises avoiding bathroom selfies, bikini photos for women, or topless shots for men. Make sure to include a few full-body shots, pictures that clearly show your face, and always use recent photos. Don’t use headshots because they make you look stiff and boring. This isn’t LinkedIn!

tinder profile bio

2
Keep the Bio Brief

You want to give someone a sense of your personality, but you also want to retain a sense of mystery, so don’t give everything away. Looking at my bio, Sameera thought it was good because it was short, but gave a basic sense of who I am and, again, made it easy for someone to message me based on the information I provided (“What kind of jazz do you like?” What’s your favorite whiskey?”).

She did, however, suggest I remove “Oxford graduate” because it sounds boastful and that can be a turn-off to people. She suggested I let men figure out I’m smart by talking to me instead of spelling it out for them. In general, she advises people avoid listing their degrees, accomplishments, and education. And for more great dating advice, know that these are the All-Time Best Dating App Opening Lines. 

phrases men over 40 should stop using

3
Don’t Write Anything Negative

The final thing that she asked me to cut was the line that says, “Really don’t care how tall you are.” I put it in there to show that I’m not superficial, which Sameera realizes, but she said that it can also come off as negative, and you want your profile to exude positivity.

In general, her advice was, “Use some sense of humor, of course, but nothing negative and don’t try to explain why you are there. You are on the app or dating site so take responsibility and don’t whine! No one likes whiners!”

For what it’s worth, being negative is on our list of The 12 Biggest Dating Profile Blunders Men Make.

the league dating app

4
Try Newer Apps

One of the reasons that I periodically try online dating again is because you meet happy couples all the time that met on an app. But I notice that I often hear them say things like, “We met on Tinder, back when it was good” or, “We met on Hinge, back when it was good.”

It seems like the trend with dating apps is that the first few cycles of people who join are actually cool people genuinely interested in a relationship, but the latter waves are ones just looking to hook up. Sameera agrees with this, which is why she suggests trying new apps on the market.

A good one is The League, which started out as an “elite” app for Ivy League graduates, and has since expanded to people who are simply smart and driven. She’s also heard good things about a new app called Cheekd, which uses a cross-platform low-energy Bluetooth technology to match you with people who are in your direct vicinity. She’s not a fan of Bumble, which she believes “makes men passive and lazy when they were already passive to begin with.”

50 compliments

5
Older People Should Try Online Websites

Sameera’s older clients have had more luck with online dating sites rather than apps, in part because there’s a wider selection of people above a certain age. They’ve had particularly good success with Match.com, which has been around since 1995. Remember, just because you’re over 65 doesn’t mean you have to close up shop. As one recent study confirmed, there are plenty of older people who have great sex lives.

If you do want to go with apps, check out The Best Dating Apps if You’re Over 40.

man on smartphone Life Easier

6
Ask Something Specific In Your First Message

As the saying goes, “You only get one chance to make a first impression.” Don’t waste it with something generic like, “Hey, how are you doing?” Ask about something that intrigues you in their profile. But be earnest. Don’t ask about their dog if you hate dogs, or what books they like to read if you don’t care about books. You’re looking for something you can connect on, not just a way to get in the door.

Fancy dates Being Single in your thirties

7
Go On Several Dates

Sameera agrees that the paradox of choice is one of the biggest problems engendered by online dating. “Endless options have kept more people single today,” she once told me. “Everyone thinks the grass is greener on the other side, and that there will always be another option around the corner.” As a result, people have unrealistic expectations, and if they aren’t completely blown away by someone on a first date, they will write them off in favor of going out with a new person, thereby throwing themselves into an endless cycle of first dates.

To combat this, Sameera suggests going outside of your comfort zone and dating people who you might not normally like, and going on several dates before you make up your mind.

I know someone who went wasn’t into the guy at first and, by the seventh date, she really clicked with him,” she said. “Now they are dating exclusively. We live in a society where people are so easy to say no to. Get to know the person.”

For tips on what not to say on a first date, check out The 17 Worst Things a Man Can Say to a Woman.

50 funniest facts

8
Don’t Make Excuses for Them

One of the latest terrible trends we have to deal with is R-Bombing, and I’ve been experiencing it personally with a guy I recently started seeing. In these cases, it’s easy to make excuses for the other person, and they themselves will usually say things like, “Sorry, I was really busy,” or, “Sorry, I’m just not really good at texting, but I really like you.”

You want to be understanding, so you take what they say at face value, but it’s a bunch of nonsense. People make time for the things they want to make time for. If Obama could schedule Friday date nights with Michelle while he was President of the United States, this person can find time to respond to your text, no matter how busy they are. You can’t expect someone to make you a priority after just a few dates, sure, but you can expect them to show a reasonable amount of courtesy and respect. And not responding to someone is just plain rude, whatever their reasons. Just move on and find someone who doesn’t act like a child.

woman texting dating

9
Don’t Play Games

What goes around comes around. I complain about men not answering me or not being straight with me, but the truth is, I’ve been guilty of doing this with people I wasn’t that into myself. Whether or not you believe in karma or energy, you have to treat people the way you want to be treated. And that means having the courtesy and courage to respond to someone and politely say that you don’t want to meet up again for whatever reason. The other person will respect you for it, you’ll relieve them of frustration or anxiety, and you’ll leave a nice legacy for yourself in their mind.

40 compliments, essential dating tips for men over 40

10
Have Sex When You Want to Have Sex

I had a very frustrating phone call with a dating coach recently, who basically acted like all women need to do to “hook” a man is withhold sex until they agree to be in a relationship. This is terrible advice. With me, I always wait to have sex until I see that we both genuinely mutually respect and like each other, and Sameera agrees that this is a good formula. Sometimes people have sex on the first date and it works out. Sometimes they wait and it doesn’t. There’s no numbered rule that can tell you when it feels right. (And, by the way, recent studies have shown that you’re actually not even more likely to have casual sex if you’re on Tinder.)

single people tried of hearing

11
Don’t Be Too Eager

Sameera says that this is a common issue, especially among women.

Online dating is making women more frustrated and men are more aloof,” she said. After going through so many failed attempts, you start to see getting into a relationship as a test that you just can’t seem to pass. Looking over some texts that I exchanged with a recent guy, Sameera correctly identified this as one of my problems. I’m so tired of dating that I make myself too available to men I’m not even that sure about. It has nothing to do with the guy. It just feels like a personal failure to have something not pan out yet again, like online dating is a claw machine rigged for me to fail. It doesn’t help that I’m selective and don’t find myself attracted to a man very often, which makes someone I’m into feel more precious than they are. Sameera suggested that I stop being so understanding of men’s bad behavior. She told me to be more patient. And then she gave me a piece of advice I want to crochet on a pillow: “Separate the ego from the outcome.” AKA, don’t take it personally; this isn’t a contest. 

If you’re feeling over dating, check out these 10 Signs You Have “Dating Fatigue”—And How to Bounce Back.

make your Instagram compelling, worst dating Phrases

12
It’s Not Just You

With all of the terrible things people do to each other online nowadays, it’s easy to think it’s just happening to you, and to let that hurt your self-esteem. Doubts start creeping in. Is there something wrong with me? Why does this keep happening to me? Why does it work out for others and not me? Am I just not good enough?

Sameera has had hundreds of clients and she’s seen it all many times over. All of the stuff that’s happened to you—a guy seeming interested but then suddenly vanishing, a girl who texts a lot but never wants to make plans—happen to everyone all the time, even to people that society deem to have a “high mate value.” As someone who writes about dating a lot, and who takes care to mask identities, people frequently share their tales of woe with me.

A gorgeous lawyer friend of mine recently went on several dates with a man who treated her really well, only to then suddenly dump her for no reason. Another stunning, ambitious friend of mine sent some nudes to a guy who asked for them, only to then never hear from him again (I can only assume he died from the sexiness).

This stuff happens to everyone all the time, and it’s important to remember that. Even if it takes some time to get it right, rest assured: it will work out in the end.

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