Phoebe Jayne's Guide to Online Dating - Installment III

The Meet Up


Thanks to many Pink readers, questions have been pouring in and most are regarding the first meet up. The meet up should not be just a date, but about making a connection and getting the second date.

Once you have communicated within the dating site, feel confident your connection is not a scam, try to get a last name. Then you can google him/her before your meet up. Don’t give your full name too soon. Be vague about your profession, place of employment, birthplace, etc. Do not give your home address too soon either. Do not go to his house too soon. Use the buddy system. Tell a friend when and where you will be meeting, and text them when you arrive home safe and door locked. Now lets go out there and have fun.

Meeting: I suggest daytime hours. Meeting for coffee is best. If after work hours work best for you, an early happy hour for a glass of wine is OK, too. But make sure it’s only one drink and no more. The first date should be in a risk-free, easy to leave environment.

What to Wear: Don’t let your first date attire ruin your chances for a second date. What you wear is a perfect opportunity to present who you are before you say a word. Consider the weather, location and time of day. Don’t try a new trend, or get a costume-like outfit. Stick to your true style. First impressions are quick to be made, and set the tone for the entire date. There is a difference between wanting to look flirty and sexy and leaving nothing to the imagination. A good rule of thumb is to choose one area of your body you want to reveal. An above the knee skirt to show off your legs, a subtle scooped neck blouse to enhance your décolleté, or an off the shoulder sweater to feature a great neckline. Don’t reveal too much. Dress for the occasion, and leave the sloppy clothes at home. Break away from all black. Include a splash of color in your outfit.

Location of Meeting:
Pick a familiar place. A coffee shop is a good start. Make sure you visit the establishment prior and have an idea of where you would sit, how much privacy you would have and their hours. Remember good parking, seating and privacy help make the meeting smooth.

Be On Time/Put your Phone away:
Get to the location early enough to make sure you are not rushing in…and for sure, turn your phone off and put it away.

Length of Meeting:
Plan on an hour. Then plan to exit. You be the one to end the conversation first.

The Bill:
Always go “Dutch” on the first date.

Before the “meet up” re-read your profile, and for sure, re-read his/hers.

You need to talk about serious topics when you are dating, but on the first date it’s important to keep the conversation pleasant and positive. That’s why reading his/her profile is important. Ask about their passions/hobbies. Avoid subjects on religion, politics, or money. Don’t try to be anything other than yourself. If you have been honest on your profile, it’s you that has brought him/her out on this date, and it’s you he/she wants to get to know.

Be yourself. Don’t tell little white lies to make yourself more fascinating. This doesn’t mean you need to tell everything, maintain some mystery. If you are interested in a second date don’t reveal everything in the first one.

No Boo Hoos:
Avoid talking about previous relationships, problems with your boss, or workplace, or troubles with your family.

Don’t Drink too Much:
If you are meeting for a drink, only have one. Even if your meeting lasts longer than your drink, switch to a non-alcoholic beverage.

Be a Good Listener:
During your conversation don’t be thinking about the next thing you want to say. Ask him/her a question to expand on what he just told you. This lets him/her know you are paying attention and you are interested. Try to keep the listening/talking ratio as close to a 50/50 split as you can.

Finding the Chemistry:
Being compatible isn’t always enough. I think you can usually tell within a few minutes if there might be chemistry, but to find out for sure, probe a little with some questions. Yes, you have to keep things pleasant but that doesn’t mean you need to avoid meaningful conversation. You could start with questions like, “What things make you happiest?” “What do you love about your work”, or “ What are the most important things in your life?”

Positive Body Language:
If you want a second date show encouraging body language. Sit close, lean in a little when he /she talks, make good eye contact and SMILE.

  If the chemistry is right, sparks may be flying. You may be tempted to make that first date a sleepover. It’s not the end of the world if it happens, but if you are really interested in him/her rein in your libido and date smart. Get to know him/her better before you hit the sack. Waiting is great foreplay, gives you confidence and boosts your self-esteem, plus sex too soon clouds judgement.
When it happens, the No. 1 rule is ALWAYS USE PROTECTED SEX, no exceptions.  Stop at the drug store and pick up a travel packet of condoms and keep them in your purse. Men should never leave home without them.

Ask for a SECOND Date:
If you are interested in a second date, don’t be shy. Ask for one. You might say “I had a really nice time, and I’d like to continue the conversation.” Be fearless. If rejection is coming, it’s coming, but if you feel a spark, it’s likely he/she does, too.

Follow Up:
  If you had a good experience with your first date and don’t feel comfortable asking for a second, at least follow up with a text saying how much you enjoyed the meeting.

First dates can be awkward, but if you have had a few conversations prior to the meeting, feel comfortable on the phone, have googled him/her and feel certain it is not a scam, and follow the above tips, you have a good chance it will be a nice meeting whether it goes to a second date or not.

Technology-Dating and Social Media tips:
  With the environment of instant messaging try to keep a sense of mystery. Remember the old saying, “You always want something you don’t have.”
Don’t make yourself so available. Never answer texting immediately. Periodically go dark for a couple of days. Read your messages but don’t answer right away.

You might even turn off your location GPS on your phone. If you are on you know what I’m talking about. is one of the highest technological sites. It uses your location to alert that other members are near by, using pop ups of who is currently crossing your path. Kind of creepy, but it’s where we are headed.

KEEP Your Self Esteem intact: Once you have a second date and you start a relationship, keep your self-esteem in check. If your date makes you feel foolish, or puts you down, do not continue no matter how good other things are going! You are worthy of more, even though you may not think so. Hold out for someone who lifts you up rather than putting you down.  

Ghosting: Once in a relationship your partner may just disappear without any explanation. This is called ghosting. Better not to pursue. The pain of not knowing why is usually easier to accept than knowing why the abrupt departure happened. Just move on. Continuing to search for the reason by calling, stalking, or texting will waste your time and block your view from the next relationship.

Complaints: The most complaints about first meet ups have to do with deception. The No. 1 complaint is the person looked nothing like his/her online photos. They were older, heavier, or less agile.

One reader said her date came in with a walker and looked ten years older than his online photo. Another stated her date had visible scaring on his face and head, yet his on-line photos showed nothing. A man said his first date had to have been 50 pounds heavier than her photos. Another looked so different because his hair was long in person, yet the photo showed super short hair. The difference was so much she passed him at the coffee shop and didn’t recognize him. Another complaint was dress. One woman said her date looked like he just came from washing his car. One businesswoman, who scheduled a coffee meeting on her lunch hour, said her date came dressed in sweaty gym clothes and he said he just came from a work out. Yuck!

I can’t stress enough to use up-to-date photos on your profile. For the first meet up, dress appropriately, and use good hygiene. You never get a second chance to make a first impression!

How long to stay online dating? Give yourself a full year. In a year, even if you haven’t met Mr. or Ms. Right, you should have an inventory of dateable prospects. Then take a break, removing yourself from the sites, and making sure they do not have permission to use you in their advertising. Revisit three to six months later.

Dating is work, navigating the sites, keeping your profile fresh, corresponding, weeding out the scams and losers. BUT don’t miss out on something that could be amazing just because it may also be difficult.

Compatibility and companionship should be the ultimate goal, but never forget the person you must be happiest with is yourself.

Enter Elizabeth (A/K/A the guinea pig):Dating0418 2

I am two months into online dating boot camp, and you’re not going to believe it: I met a man I really like. We have been on three dates with a fourth scheduled for this weekend. As much as I promised Phoebe Jayne not to put all my eggs in one basket, I haven’t checked my online dating sites since my first date with…I will call him Mr. Pecan.
If you recall, last month I wrote: “Online dating is like a can of mixed nuts, without the less-than-50-percent-peanuts guarantee. You really have to pick through for the good ones…like the pecans. And, there are very few pecans.”

Guess what? I found a pecan!

Mr. Pecan is from my hometown of Columbia, SC. He is two years older than me and a true Southern gentleman. Our first date was at the Hilton Head Wine and Food festival Grand Tasting, (Great news! He knows wine.) where I broke Phoebe Jayne’s rule of having only one drink. For heaven’s sake, it was the Grand Tasting, and one never knows exactly how many glasses of wine those little, delicious tastes equal. We pretty much hit it off immediately. It felt like I’ve known him all my life—probably because we were raised similarly and have many friends in common. (Why did no one think to set us up?)

He met a ton of my friends at the Grand Tasting, and afterwards we went to dinner and then met more friends at Porter & Pig to watch The Chiggers—my favorite local band! (Be sure to read about Jennifer, the lead singer, on page 24.) Mr. Pecan was game for hanging out with my friends, and again, he fit right in. He is personable, kind, thoughtful and funny. Who doesn’t want to hang out with someone like that?

The next morning, I held my annual Wine Fest Pre-game Breakfast Party with around 16 guests. Mr. Pecan arrived with all the fixings for Bloody Marys. He helped in the kitchen some, talked to everyone and had no need to cling to me. In other words, Mr. Pecan knows how to socialize, converse and accommodate—dreamboat! Not to mention he is handsome and tall—very tall—and funny.

While all of this sounds wonderful—and it is so far—there have been a few “side-effects” I didn’t expect. Wine Fest weekend has been a big event for me for years. Lots of friends come to town, many stay at my house, the big breakfast party—it’s just one of my favorite times of the year. Needless to say, on Sunday afternoon, when all my friends had left, including Mr. Pecan, I felt a little empty. Normal after an exciting weekend, but this was more. I got kind of sad…and scared.

I realized I had shut and sealed the door on needing or wanting a man in my life. It dawned on me how independent I have become. Girl Power! I orchestrate my days, how I spend my time. I decide single-mindedly the who, what, when and where in my life. I do this to shield myself from being vulnerable. I do this to never again have to go through what I went through last year—no more sitting duck.

I don’t know what I thought online dating would be like. I think I didn’t allow my mind to wander that far. Perhaps it just meant I would have a date to the Heart Ball next year, or someone to get a drink with on Friday night. However, that Sunday afternoon, as I lay down on the sofa, insecurities I was sure I had bagged up and thrown away came flooding back.

I wondered if Mr. Pecan liked me. Would he call? Text? Will it be like college when a guy said he would call and two weeks go by? I thought of all the reasons why he may not. I wondered if I said the right things. I questioned if I had “played the game” correctly. (I am not a game player) Did I seem too into him? Or, maybe I was too aloof? I can be that way some times. I felt like a teenager. Doubt sliced through my airtight shut door like a chainsaw. What is all this? Why did I open myself up to this again? I am going to get hurt. I am setting myself up for disappointment. ALL these emotions raged through my mind.

A few deep breaths, and I regained my discernment. A few minutes later, a text. Mr. Pecan. I do what I do best in my unwillingness to play games: I tell him my thoughts. He responds: “To find love you have to have a willing and vulnerable heart.” I take in a deep breath of relief. He is right. He understands.

He then adds, “You can quote me on that.” I laugh. This dating stuff may be nuts, but when you find a pecan, it’s definitely worth at least opening the can.

If you have specific questions about any of the above, feel free to email your questions to This email address is being protected from spambots. You need JavaScript enabled to view it..
In addition, Phoebe Jayne is currently gathering testimonials for her upcoming online dating workbook and would love to hear your experiences.


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