I Asked 6 Dating Experts To Tell Me Why I'm Still Single (GULP.)


I bit the bullet and asked for tough love dating advice.

I’ve always been intrigued by the idea of dating coaches. I’m actually friends with a few of them (it’s a small dating and love world, y’all) - and I love learning how they coach people to find love. Since I consider myself to be a pretty active, able and positive single gal, I never thought I needed the professional services of someone to teach me how to date…but I was curious about their expert advice on playing (and eventually getting off) the field.

So I decided to turn the tables and have a few love & relationship coaches interview ME instead of the other way around. These folks asked really tough questions about who I am, what I want and what type of guys I date and gave me tough love advice that maybe - just maybe - will land me a boyfriend.

Here’s what six dating coaches think I’m doing wrong in love:

1. I’m being too aggressive.

According to Robin Gorman Newman, founder of LoveCoach.com and author of How to Meet a Mensch in New York and How to Marry a Mensch, I need to be a little softer with guys and let them come to me. In fact, almost every expert told me that I should give guys more of a chance to pursue me instead of the other way around. “The guy should always be the one to take the lead,” Newman said. “I wouldn’t advise for you to initiate because it makes the relationship too familiar too fast.” Newman also mentioned that it’s fine for ladies to go up to guys at bars or in social events, but to never take their number or text them first.

My reaction: I really, really hate dating rules , which is why I don’t have a problem reaching out post-date if I feel good about it. That being said, every single time I've made the first move, I’ve never ended up dating the dude. Maybe it's time to hold the iPhone trigger?

2. My career is a huge turn-off.

Look, I know writing about love and my dating life on my blog isn’t exactly a welcome fact to reveal to guys on dates. (In fact, I don’t really tell them about it until the third date, but hey, don’t judge, I never use real names!) San Francisco-based ThreeDayRule.com matchmaker and dating coach, Carla Swiryn thinks my tell-all dating stories could be keeping me from a relationship. “It makes sense that men could be apprehensive about being with a woman or even going on dates with someone who writes about dating for a living,” she says. “But the right man for you will be so excited that he won’t care.” She also noted that if and when a guy reads my blog, it might seem like I have a long list of standards and things that I don’t like - as opposed to things I do - so it might be a good idea to diversify my writing. 

My reaction: Happy to know that the thing that makes me the happiest (writing and inspiring others to believe in love) isn’t going to be what prevents me from getting a ring put on it. It isn’t a bad idea at all to write more about what I dig about men, instead of what pisses me off. 

3. I go on dates too quickly.

My cardinal rule with online dating is how I feel in a public restroom: get in, do your business and get out. I always try my very best to speed up the conversation to get to the happy hour portion instead of wasting time on apps and sites. But Laurel House, dating coach and author of Screwing the Rules, says that I need to take more time to get to know guys before I give out personal information. She also says - gulp - that I need to talk to them on the phone. “This is where you will start having what I call core value conversations,’” she says. “These are substantive conversations that show and tell who you are through stories that reveal how you got there.” From there, she says, people connect through storytelling, and if we don't click on the phone, I shouldn’t waste my time in person.

My reaction: OH MY GOD. I get knots in my tummy just thinking about having to talk to some guy that I don’t know on the phone. I don’t even really like talking to my friends on the phone but a dude I haven’t met? So much anxiety. I vow to give this a try, but it makes me insanely nervous. (Why is that? Didn’t I used to talk on the phone for hours when I was 12?)

4. I bow out too quickly.

Maybe because I’m busy or frankly, been dating too long and get bored, I never really give guys more than two dates before I decide I’m over them. April David from CupidsCronies.com says I’m missing out on a lot of potential boyfriends this way. “How many interviews have you been in where you believe the interviewer really knew who you were after an hour?” she asked. Valid point, April! She said that my ‘we didn’t have chemistry’ excuse is bullshit: “Real chemistry is more than just being able to have a good conversation and attraction. It’s having similar values and commitment to not only the other person, but also the relationship.”

My reaction: Yeah, yeah, yeah. I get what she' saying; I just kind of hate it. I guess I still have this overly idealistic idea about how it’ll feel when I meet this person and if I don’t get that somethin’ in my gut from the beginning, I have a really hard time believing I’ll feel it after another handful of dates. But maybe … I’ll give it a try. (Again, thanks mom and dad for those unrealistic expectations!)

5. I’m still hung up on the past and blocking love.

I have to admit, I was most excited about talking to the dating psychic! I’ve been to clairvoyants before and I’m the daughter of an astrologer, but there’s something fascinating to me about people who can supposedly predict the future. Alexandra Chauran from EarthShod.com only asked me my birthday and then did something called ‘scying’ which is the act of looking for imagery with a tool and reading what it says. She saw two older people (possibly parental figures) holding hands but standing apart, as if their arms made a doorway. She says that I need to walk through this doorway to find love. “Rather than being hung up on the past or exes, you need to move forward,” she says. “If you don’t make that new beginning happen, you might find yourself sabotaging your chance at changing your single status.”

My reaction: Hmm. I mostly feel over my ex-boyfriends, though I do sometimes have feelings of inadequacy when I think of them or how we ended things. (I especially get jealous when they move on to new girlfriends.) Perhaps I need to make more of an effort to not compare myself and to believe that the relationship went wrong because it wasn’t right, not because I was in the wrong.

6. I don’t know what I want.

The last person I talked to was the person I consider the ‘expert’ in my life. She’s one of my best friends, a fellow single lady and really, the big sister I’ve never had. She’s the queen of tough love and telling it how it is so I know she’d be honest with me about what she thinks. Her opinion? I need to do some soul searching instead of all this dating: “You very much want to be with someone, so when someone wastes your time you get irrationally annoyed, but a little taste of being happy is enough to make you go crazy with the texting and hang on much longer than you should,” she says. “I think you’re at a point in your life whren you need to think hard about who you are and what’s important to you.” She suggested that unlike the lists I make about all of the things I want in a guy (and all of the things I don’t), I need to make a list about me: my strengths, my weaknesses, my character traits, my desires and figure out what it is that I really need in a person to balance me out.

My reaction: Holy sh*t! As I’m reading her advice, I can imagine the relationship. I can imagine the guy. But I’m nowhere in the picture. In the countless dates I’ve gone on the past year, I don’t know when I last stopped and thought: Well, what’s going on in your head? What is it about me that makes me a good partner? The focus shouldn't be on dating… it should be on me.

The biggest thing I learned from all these coaches? We all have things we can improve on, be better at, learn from and do differently. I definitely will be making some changes, including figuring out exactly what it is I want in someone, but it's also about accepting who you are and where you are in your life. Sometimes I'll be aggressive, but it's okay if I'm soft sometimes, too. I might go out on too many dates, so I shouldn't ever feel guilty about my Netflix evenings, either. Ben & Jerry's and wine, anyone?