Archives for posts with tag: dating

The first hour into an eight-hour international flight I started to feel anxious. My mind was reeling and it wasn’t a fear of flying. I had been seeing a guy for a month and I was happy but something felt off. My trip was planned for ten days so I would have to wait until I returned home to address my uneasiness. In the spirit of full disclosure, I knew he was seeing someone when we met but alas, many relationships in my city/generation start that way. When you start seeing someone they might be seeing other people and if things go well, you could end up dating exclusively a few months in after the “conversation.” How long can you hold onto the monkey bars? Longer than Suzie? Congrats! You win? If you’re reading this Mom, yes, I know it’s upsetting and far from ideal.

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“… loneliness allows us to look honestly and without aggression at our own minds. We can gradually drop our ideals of who we think we ought to be, or who we think we want to be, or who we think other people think we want to be or ought to be. We give it up and just look directly with compassion and humor at who we are. Then loneliness is no threat and heartache, no punishment.” -Pema Chodron

A man asked me to go on a second date with him and I politely declined. His response via text message was comical but it came from a place of loneliness. Our first date involved a few casual drinks and the need-to-know details. “Guy from Queens” was kind and straight-forward, things I admire, but I saw a few warning signs in the details he chose to share about his life. He mentioned that he recently broke up with his live-in girlfriend of five years. Then quickly added that it had been ten months… He was now living with his uncle, an intense divorcé and wanted to move out but he didn’t mention an action plan. I don’t fault him for it, but I sensed during our first date that he was already hoping I might be the person he would be moving in with. It’s nice to want to fall in love and you should go into any relationship with an open mind but you also need to be aware that things can get messy FAST. Trust your instincts because loneliness will not lead you to the best decisions. Eff the funk and make peace with being lonely.

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Next March, my cousin Rachel will walk down the aisle and say “I do” to her fiancé Bryan. She’s one of three women I know who met her husband through a dating website. Pretty darn cool.

In reality, dating websites can be a lot of work (trial and error) and the experience can be discouraging. The whole goal is to get you out of your love funk, not push you further in so Rachel has agreed to share the 411 on what worked for her.

 The lovebirds: Bryan & Rachel


Q: How would you describe your experience with online dating before you met Bryan?
A: Honestly, I went out with a lot of really nice guys with only a few losers and weirdos thrown in to make for some good stories but it was hard finding a nice guy I was excited about. As someone once told me, “you’re not buying a horse.” Just because someone was nice, had a good job, a car, loved his family, etc., it didn’t automatically mean we had chemistry.

Q: How many dates do you estimate you went on total?
A: I would say around 50 over the course of a couple of years.

Q: Which dating site did you use? Positive/negative things about the site?
A: I was on and a free site called I found that I preferred My theory was that if the guy had to pay for this, he was taking it more seriously. Also, has a “looking for an intimate encounter” box that a lot of guys checked and was an immediate turnoff.

Q: What is your best piece of advice for someone who is new to online dating?
A: Go on lots of dates. It’s a numbers game. Like I said before, I met a lot of really nice guys but had to keep looking until I found a really nice guy I clicked with. Also, always talk on the phone at least once before you go out. It’s amazing how much you know about a person after a phone conversation. If they seem awkward on the phone, a date will be torture!

Q: What was the biggest learning curve you had to adjust to?
A: I had to remember that I don’t really know these people or what’s going on in their lives and I had to stop taking things personally when they didn’t work out. My exact words after my first date with Bryan were “he was nice but I’m not going to hear from him.” I was on a date with someone else when he called two days later.

Q: Which activities are ideal for a first date with someone you meet online?
A: I always liked going to dinner. If we hit it off, we went for drinks after, if not, “thanks for dinner!” After all of those dates, only one guy ever made me pay for my own meal so I was always up for a free dinner. If you’re not sure about the guy, keep it shorter and go for coffee.


Lots of people like the beach and Italian food. Who cares? Unless you surf regularly or make a mean meatball, someone reading those facts in your profile will breeze on by without a second look. Figure out what sets you apart from the crowd and then promote it. You are a brand and you’re searching for your target market.


-Be honest with yourself and your potential matches

-Present yourself in a positive light

-Post at least three photos

-Make an effort to separate yourself from the crowd by showing your “best side”

-Edit your profile if you aren’t catching any fish

“Do” for profile photos: geek out/ham it up a bit to show your personality, appear to be approachable, leave a bit to the imagination when it comes to clothing

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-Be rude. If someone sends you a message and you aren’t interested the standard is to not respond or respond with a kind “Thank you, but I don’t see us as a match.”

-Post unflattering photos (think about lighting, wardrobe, etc)

-Be offended if you initiate contact and the other person isn’t interested. Do you want to force yourself on someone or find someone who wants to pursue you?

“Don’t” for profile photos: wear sunglasses indoors, wear work clothes/seem too into yourself, make it look like you aren’t interested in monogamy


Try to keep in mind that stock at a start-up company doesn’t appreciate overnight. We can’t all be Google. You need to make it clear to the public that you’re ready to engage and then prepare to grow from the resulting experiences. Now get out there!

Additional references: Remember Priya from the MBA post? She heard I was writing about dating and recommended I read the book “Attached” by Amir Levine and Rachel Heller. I haven’t read it yet but that shouldn’t stop you!