Ask Him Out! Here’s How.

The tables have turned. Women are in charge, there are now even dating apps that immediately put the ball in our court to open the conversation with a man of interest. So why not do it on the street?

I was 24 years old. One morning, I went to breakfast with a friend. I noticed a man with olive skin, and slightly longer hair that took my breath away. My friend said that I should say something, but I was too timid. I couldn’t concentrate, I couldn’t eat anything; there was just something about this guy. My friend finally decided that she was going to say something. She walked over to his table and told him that her friend was interested in him. He asked “What friend?” She turned around and I had jumped the fence of the restaurant and was hiding in a clothing store next door. “Uh, she was just here, anyway, here’s her number…”

He called. We arranged to meet that night. He ended up coming to a Comedy Show I was performing at. He joined to grab a bite with all the comics afterwards and ended up picking up the entire bill. Thus began the passionate affair with a serious gentleman that lasted for the next three years. (I know this would be better if I said “ …and now we’ve been married for x years,” but it was a significant relationship and an experience that I learned a lot from.) He totally Pretty Woman’d me (except I wasn’t a prostitute, just a young, nerdy kid). Regardless, the relationship helped me bloom into the woman I am today.

That is an example of what can happen when you say something (albeit it, my friend spoke on my behalf). This was in 2006, it is now 2015, and fewer and fewer men have the gumption to approach a woman in public. The tables have turned. Women are in charge, there are now even dating apps that immediately put the ball in our court to open the conversation with a man of interest. So why not do it on the street?

How many times do you see someone in public that you find cute but are too shy to do anything about it? The next time you are on the elevator with someone that peaks your interest, or see someone at a coffee shop, just walk up to the guy and introduce yourself. What do you have to lose? It’s so easy to hide behind your computer screen or be glued to your phone that you could in fact miss an opportunity right in front of your face. Look up folks! There are men everywhere; who says we can’t speak to them? I know, it might seem super creepy and weird at first, but it’s actually not that bad. Turns out, guys are really easy to approach. THEY LOVE WOMEN and don’t mind talking to us!

I have since been helping friends have the confidence to approach men and have two relationships under my belt. Most guys think it’s sexy and a turn-on, very few feel “intimidated” by it and come on, who wants a guy that feels intimidated by a woman anyway? Confidence is always attractive regardless of gender. It shows that you aren’t afraid of failure, and that is a great quality to have in life.

How about you? Do you make the first move?

Looking for Love on a Trail of Breadcrumbs

I had a really great first date with a curly-haired breadcrumber who kept in sporadic touch with me, which made me sad because I really had fun on our date and wanted to see him again.

There are lots of ways that technology has changed the way we interact with each other.   A few years ago, if you’d been dating someone and you didn’t want to anymore, you had to say “hey, thanks for dating me, but I don’t want to anymore.”  Now we ghost, fade, or breadcrumb our way out of hard situations.

Ghosting has been well documented: you’ve gone on a not-insignificant number of dates with someone, more than two or three, and then you Keyser Soze them like in Usual Suspects- you’re just in the wind.  No text, no call.  Everyone hates it, but everyone does it, because we feel that having been ghosted implicitly gives you permission to ghost, like being bitten by a werewolf makes you one yourself.

The first time I was ghosted, it really took me by surprise.  I assumed that the person I had been dating for nine months was in rehab or prison (either one would have been a pretty good idea), and when, after two weeks of silence, I saw him tagged in a photo of just hanging out in his favorite bar, I was pretty amazed.  I didn’t call it ghosting, I called it “being dumped by a sociopath”, which is in many ways more accurate.

Ghosting happens because it’s the easiest option, there’s no confrontation, and sometimes, ghosting happens because it never really closes the door- in the ghoster’s mind, they’ve never really broken it off with you, so there’s still a possibility of dating you in case what they’re pursuing also peters out, and also the thing after that, or if they someday reach the end of Tinder and it’s just a picture of a cat with a colander on its head.  Breadcrumbing is the same- they might not want to date you now, but they maybe want to later?  Or not?

3 Ways to Date Yourself

Being single can make you feel sad sometimes. We’ve been conditioned to believe that love is the most important thing in life, and maybe it is!

But, that love can start with us. We can delight in our company! So, in your loneliness, I propose dating yourself. Yes. I said date yourself. Take you out. Love you. Here are three ways you’re probably already doing it, but now change your mindset and the way you go about them:

  • GO TO A MOVIE! Make it cathartic

I went to see Fences and I cried. It made me realize that I wanted to watch sad movies! There’s a catharsis in them. You get lost in this journey with these people and whatever pains of the day are buried in you can be released in the end. I recommend watching the movie in the evening after the weight of the day has worn you down, you could just get lost in the lives of other and then sleep. My goal is to check out Moonlight and maybe even Manchester By The Sea (ew Casey Affleck) just because I hear they are beautiful which is code for you’re probably going to cry. And if we can’t cry away the expectations of society, how will be free for good things when they come?

  • TABLE FOR ONE! Own the place.

Take yourself out to a café, or to a restaurant. Yes, go to a nice restaurant, and say you’re a party for one and enjoy a nice steak dinner, or something vegan. Whatever floats your boat. It’s important to enjoy your own company. It’s important to understand that your validation is not with whom you share your company with. You’ve got to be happy with you and not feel embarrassed that other people may pity you. And if they do, so what? Eat your nice meal. But, if a steak dinner is pushing it, café spots are cute to spend some quiet time. I don’t mean Starbucks, but the quiet little café somewhere in a less crowded part of the neighborhood. You go without your laptop, and just enjoy the ambiance, cakes, or spinach crepes they have. And of course people watching!

How Did You Pull That?! What I Learned from Dating a Male Model and You Can Too.

There is a special sort of prestige that comes with dating a model.

When I first moved to New York a couple of months ago, I matched on Tinder with a guy who listed his occupation as “male model”, and judging from his photos he wasn’t lying. Even Ray Charles could have seen the man was beautiful. I was intrigued he found me as attractive as I found him attractive, but did my best to not let my insecurities get the best of me. So I allowed Model Boo (his nickname to protect his identity) to get my number so we could get better acquainted.

I showed his photos to several close friends of mine (both male and female) and the consensus was “HOW DID YOU PULL THAT?!” Honestly the answer wasn’t being myself because Model Boo would always tell me how he thought I was hot, but I still said it was my sense of humor. “Keep him around as long as possible,” my friends would urge me. Even Model Boo would tell me to not let him get away.

It was all rainbows and butterflies in the beginning. We’d see each other often, and he’d text me all day long. I model myself, so I’d constantly talk about the industry with him. It was good to talk to someone that knew and understood some of the things I encountered on a regular basis. And even though models have reps about being terrible in bed, Model Boo really knew how to work his love muscle. I was definitely satisfied.

But then, things started changing. I started hearing from him less and less. He started to be less and less generous. And then he did something to me that was the straw that broke the camel’s back.

Model Boo had asked me to spend the night at his place so we could have morning sex the following morning. I didn’t have any plans, so I agreed. The morning after I slept over, I am in his bathroom showering and I hear the sound of cooking commencing in the kitchen. I’m thinking to myself “Oh how great he is making breakfast for us!” Well, I leave the bathroom and come out to find a dirty dish and pan in the sink. No food in sight. Apparently, Model Boo thought only he was worthy of nourishment in the AM. I was nothing short of seething. This is one of the top five rudest things I have ever been on the receiving end of. How does one have the heart to do this? As I left his apartment I just knew that this was unforgivable and I was never talking to him again. So as soon as he was out of my sight I blocked his number.

Why Speed Dating Is Working for Me Today

About six months ago, I was hired to be a host at a speed dating event. As someone whose prior (and sole) experience involving speed dating was based on the movie Hitch (moment to swoon over the thought of Will Smith please), I was more than a little apprehensive when I agreed to take the job. Call me crazy but I just don’t love getting involved in things I don’t fully believe in. But it was a job and it paid, so I convinced myself to give it a shot. I figured if all else failed, it would make for an interesting story, and that was enough incentive for me.

As the event neared, and I had spoken in great length with the organizer (who lives out of state, hence hiring me to represent her business) I became even more skeptical. Here we had close to 30 participants registered, and then me, slated to run the whole thing, even though Will Smith hadn’t returned my calls and by the looks of it, wasn’t going to attend. Bummer. As prepared as I was to host the evening, I didn’t know what to expect.

A Delightful Dating Surprise

Cut to the event and the delightfully surprise ending it had. In the end, less people attended than had registered (I’m sure the pressure got to them, which I understand!) Yet of the people who were in attendance, these were some of the most interesting people I’ve ever met. Everyone was so open to the idea of meeting someone, which led to some of the most genuine and kind conversations I’ve yet to witness. Also, as all participants were in the same boat as they arrived and no one really knew what to expect, it was really easy to find common ground and connect with each other.

The event turned out to be a pleasant surprise for several reasons. One, it went off without a hitch (see what I did there- Hitch?) and everyone really enjoyed themselves, so from an organizational standpoint, it was a success. Two, as we had more men than women registered, I was happy to chat with the extra man each round and make sure he felt comfortable. In doing so I found myself involved in really interesting conversations with some wonderful men. And three, it helped me to see that I truly had nothing to be skeptical about, and left me with a really great impression of speed dating. I’ve hosted two since, and will continue to host as it fits into my schedule.

Why Speed Dating Is Interesting to Me

Fashionable interracial couple drinking wine during date sitting at restaurant having romantic evening and nice conversation raising glasses to love at first sight. Hipster man proposing toastNow, should I try it myself? Here’s why I think speed dating is a really interesting concept in today’s world. With technology as predominant as it is in every single facet of our lives (I just downloaded a meditation app this morning) we are ultimately trying to make the most of our time, right? I, for one, constantly find myself telling people “there’s an app for that”. Our time is so precious, and we’re all simultaneously trying to hold down a job (or two), maintain a fitness regime, a social life, run errands, prepare meals, etc. We have so much to do that meeting new people can become really daunting. After a day of working two jobs, fitting in a workout and going grocery shopping, I personally, just want to crash on the couch and binge watch Master of None.

Two Months of Dating in One Night

With speed dating, in one night I can realistically do two months worth of dating in one night. I don’t have to feel the guilt of “stacking” or “double booking” dates because the event is literally designed for that purpose. And there’s no pressure of sitting through an entire meal, worrying about who’s going to pay at the end, etc. I could very well go on 15 different dates; even if I connect with 2 of them, that’s great! I can still make it home for the 10 o’clock news! I didn’t have to make a plan, gather a group of girlfriends, research a good bar for singles and then spend a bunch of money only at the end of the night to discover that the night was a total bust.

It’s been a happy accident that I’ve been able to participate in the speed dating events as more than just a host, one that has even resulted in four dates (with three different guys). My experiences have totally changed my opinion on speed dating and I would definitely recommend it to anyone who hasn’t tried it or has been holding out. Even if the “date” is going really poorly, it only lasts 5 minutes. And who knows, maybe the next guy to rotate in will be Will Smith. If you’re lucky!

I Went on a Date Every Day of the Week. Here’s What I Learned.

7 Dates in 7 Days? I’m older, wiser (and exhausted).

Monday was Dr. Corey from Bumble. Tuesday was Grant, a setup from a fellow comedian. Wednesday was Kevin, a super hot Tinder dude from Chicago. Thursday was Chris, another Tinder guy who worked in Marketing. Friday was writer James AND creative director Logan, a Bumble & Bumble. Saturday was Sean, a guy I met at a local bar. Sunday, I rested. JK! Sunday was a coffee date with a producer. I work for YOU!

So, in the spirit of sex, romance and everything in-between, here are seven things I’ve learned about people (especially myself) after going on seven dates in seven nights (and sometimes more). You’re welcome!

Drinking Dates Are Great (But Be Careful)

romantic dinner

According to doctors and any non-alcoholic, I drank way too much last week. Way too much. And no, it was not healthy. I’m a big fan of the happy hour date (cheap, and I love a cocktail to ease any awkwardness) but if you’re going to date a ton, stagger those date activities! I’m a gal who can definitely handle her booze, and even I was negotiating what I’ll lovingly call “Pinot Fatigue” by Thursday.

Be Aware Of Repeating Yourself (Or Forgetting What You Said)

Couple Dating

There’s so much backstory and chat built into a date- when you meet, when you text, the lead up, the conversation after- if you’re going on a bunch of dates all at once or just one every once in a while, review your text chain before you meet up to make sure you know exactly what they know about you, and what you know about them. Believe me, it can be embarrassing when you say, “So, what was it like growing up in Jersey?” When they’re from the Bay Area. Cool move, Rebecca. Cool move.

Be Thorough About Hygiene

Beautiful woman standing at the shower. is washing her hair.

I know you’d do that anyway, but when you’re meeting a bunch of new people in such little time, you’ll want to be hyper-vigilant about this. Depending on who you are, you probably wear makeup, or product, or something when you go on a date. Well, if you’re going on one date a day, you’re going to be doing a lot of prepping, making up, eyelining, cologne-ing, etc. So it’s really, really important to shower regularly and make sure you get ALL the makeup off upon the conclusion of your evening. Nobody likes to show up to a date with the person looking raggedy AF. Am I right?

The Blowout Is Your Friend

Young man paying a compliment beautiful woman

That being said, one distinct hair style for dates will cut your anxiety-laden prep time in half! I’d suggest a blowout or a flattering go-to ‘do to have in your back pocket (mine was wavy, my hair’s natural texture, with a cute, high ponytail) so it’s one element of the date you just don’t have to think about or roll the dice with. There are lots of decisions to be made on dates- place, time, how many drinks, what to wear, if you should drive…your hairstyle doesn’t have to be one of them!

Dating Is Expensive (Even With Gender Norms In Place)

Young man and woman drinking something at a cafe

I’m definitely a pay-my-way kind of gal, and while most of the men I went on dates with paid, there was definitely a financial cost to this “experiment.” Drinks, some of the time, of course. And food after you got a little too drunk (cough cough, Bumble & Bumble Friday, cough cough), and gas if you’re driving across town or worse, taking Lyft, Uber or a Taxi. There’s also data charges on calls if a date is really into texting (though admittedly that was less of a concern than my 3 am Taco Bell run). So if you’re going to date and not go full diva by demanding the other person pays or always drives your neck of the woods, prepare to take a hit to the ‘ol Wells Fargo.

The Cream Will Rise To The Top

couple picnic date

When you’re dating a bunch of people, it’s really, really easy to compare conversation, humor, behavior, attractiveness and kindness. You’ll know right away which people are worthy of a second date much better if you’re dating a LOT, and if they’re proactive enough to keep the momentum going. Keep inventory of this! Don’t second guess your gut. You have many options when you’re going on seven dates in a week or some such crazy dating binge (who would do that? An insane person!). In this case more than others, you should never feel desperate. Ever. People are everywhere and you, my friend, are a queen!

People Love Questions

Cute Couple Feeling Curious While Choosing Some Desserts

If the date is going super well or becoming a trainwreck (that was hyperbolic, I mean, if it’s REALLY going that badly, just leave!), a quick way to not feel horrifically awkward is ask questions. Turns out, people love this, it always keeps the convo going and it will take you from treading water conversationally to back into the game. It’s a no-fail way to seem desirable, social and in control. Sexy qualities, grasshopper!

Four Times My Emotional Intelligence Helped Me Make Smart Dating Decisions

Because sometimes your IQ isn’t enough.

Dating in 2018 can be tricky territory. Between getting ghosted, fielding unsavory Tinder hookups, and a whole gamut of other things, it’s hard to remember how to date healthily. By dating healthily, I mean being open to building new relationships and meeting new people. I also mean knowing when to end a situation that won’t give you what you want.

Emotional intelligence is a buzzword these days. While I won’t call myself an emotional genius, I can think of ways that my emotional intelligence guided my decision-making in the dating realm.

1) Be a good judge of character

On Tinder I met this man, once. He had a beautifully bushy beard and was extremely attractive. On our first date we met at a bar in December, sitting near an open fire. We talked, but really, HE talked. A lot: about his daughter, about his Ph. D program, about his undergraduate experience, about his studies in Afrocentric thought. All that talking he did should’ve been a red flag. We met subsequently after and he literally charmed the pants off me. The physical intimacy was a stellar encounter that I replayed in my head for weeks. But something clicked the fourth time we met – this guy was a self-involved asshole. All he cared about was talking about his life and trying to prove me wrong at every turn. Trying to undermine my intelligence because I was, in his words, “a baby” (we had an eight-year age difference).

It’s easy to get caught up in good sex (“dickmatized” is one of my favorite words). But I do consider myself a solid judge of character, even if it takes a few dates. I read the tone of his voice when he was about to say something condescending. I read his barely-concealed sighs when I would retort with my own rebuttals. It was the body language of someone who didn’t take me seriously.

 2) Have Self-Awareness

To be a good judge of character, one must know thyself. Which means knowing strengths, weaknesses, what you want and what you definitely don’t want. B was someone I went out with two years ago. He was a sweet and chivalrous type, always opening doors and insisting on paying when we went out. He treated me and my body with respect. The problem was that we had different ideas of how often we should see each other. Once every three-four weeks was enough for him. I could have gone out with him longer, had I been looking for a noncommittal situationship. With age, I’ve learned that I’m not a casual type of girl. And I hate gray area. That sealed my decision to end things at the three-month mark.

Being alone is better than settling for what you don’t want. Having a clear idea of who you are and the things you find important should always be at the forefront of your quest for romance.


3) Know when to apologize

The learning curve was big when I was in my first relationship. He was a friend first, one that I had intensely crushed on for months before mustering the courage to tell him my feelings. I thought that would be the hardest part. Nope. The hardest part was managing expectations. Even together, I felt like I was still pining for his attention. All I could think about was the attention he wouldn’t give me. I didn’t stop to think how he might feel until we talked things out (right before he dumped me, but it was useful nonetheless). He felt like I pressured him at times. “You just think about what you want, and not what I might want.”

A light bulb came on. He was right. I apologized for my lack of consideration. Our dating was new for him too; he had never gone out with a woman before. I think about that first relationship a lot, as brief as it was. Not being able to relinquish the ego holds you back from a lot of lessons.

4) Don’t Hold Grudges

Feeling like someone wronged you hurts. I get that. My summer 2017 wasn’t the best, partially because of an almost-romance gone sour. I say “almost-romance” because we weren’t dating per se, just two friends exploring what it was to be more than friends, living in the gray “friends with benefits” territory. The things that happened between us made me see him in a different light. I found him flaky, unreliable, and sending mixed messages left and right. The tipping point was when he abandoned me at a time I needed a friend the most.

It would be easy to resend him forever, to fall into a victim narrative of how he treated me badly. Of how much he sucks and how I’ll never trust him again. But a) that’s exhausting and b) serves no one. He was dealing with some personal turmoil, and nobody’s at their best when they’re trying to keep their head above water.  I understand that. Most importantly, I understand how much lighter my soul is when I forgive him and move forward with my life.

trust him