How To Start Online Dating

A friend of mine recently posted, “My problem is I don’t know how to start dating again, lol. . .

I originally replied that “You start by starting

I realize that was pithy and cutesy, but I truly mean it. But in the meantime, I went back and dug up some notes I had prepared for a radio interview last year about online dating.

Step 1: Knowing What You Want
Make sure you are mentally ready – that you are over any bad past relationships and that you are open to actually going on a date. Know what you expect from a dating situation – what kind of dating partner you are looking for, how much time and attention you want from them, and what kind of level of intimacy you want from them. Also, know what you bring to a dating situation – what good qualities you bring, what level of commitment you are willing to offer, and how much intimacy you are willing to give. Finally, know what your dealbreakers are: smoking, drinking, drugs, sex, kids, marital status, employment, etc. If you don’t know what you are looking for, you’ll never know when you’ve found it!

Step 2: Putting the Best REAL you forward
Choose sites that work for you – there is a virtual cornucopia for you to try. Don’t try Christian Mingle if you are pagan, don’t try Trek Passions if you don’t know a Ronulian from a Klingon.

Post pictures, real pictures of yourself. When I’m on a dating site, I try to post a new, current picture every month. I’ll also date it in the caption so they know it is new. Don’t post a picture of yourself that you are not willing to live up to, and for goodness sake’s – smile! Also, please don’t take selfies in the bathroom or your car. It’s overdone and underwhelming. And although we all do a little artistic cropping, it’s often better in the long run to put yourself out there as you really are. At least one full body shot so they can see exactly what they are getting.

When completing your profile, make sure to write what you think others would like to read about you. Don’t complain about all the jerks you’ve met on the site, how your last ex broke your heart, or how you could get that hairy cyst healed if you could just get off the welfare, bondo the rust on your car, and find a job where the boss wasn’t an a**hole. Keep the drama out! Instead, talk about the good and fun things in your life: your last fun trip, favorite book you read, weekly or unique activities, volunteer work. If you can’t think of things – ask your friends!

Finally, do unto others as you would like to have done with you. If someone contacts you, and you are not interested – thank them for their time, explain briefly why you are declining, and then wish them success in their journey. It never hurts to be polite – but you don’t have to keep up a running dialogue with them. Also, if you are looking at profiles, wishing someone would contact you – go ahead and contact them! Read through their profile, find something that intrigues you and mention it. Don’t fake it though, remember, you are putting the best REAL you forward.

Step 3: Taking it Offline
Online dating should be fun, and since you are not in the same room, a more comfortable way to communicate. The computer screen is between you and them – a great buffer. But don’t get stuck in the communication trap of just talking online. If you wait too long, you’ll never move from emails and IMs to a real date – and then you are still home alone. However, move at a realistic pace. If you feel like someone is pressuring you to meet or give out personal information too fast, back up.

Typically, if I’ve been communicating several days with someone, I’ll then move to a phone call (not phone sex!) or two before setting up a date. Nothing major, just coffee or a low-key meal. Something that allows you to chat and see if there is anything real there. Remember what you are looking for, don’t sacrifice a relationship for a one-night stand, but still – this is not an interview to grill each other over – this should just be fun! If you can have fun together, you know you are off to a good start.

Step 4: Keeping it Safe
Once you get to the communicating/potential date stage, you have to start instituting the Buddy System. Choose 2-3 people that you trust and keep them in the loop of who you are meeting, where, and any info you have on your date (Pic from their profile, cell phone number, when & where you are meeting up). Designate a time that you will check in with your buddy to confirm you are safe and a back-up plan if you need to exit.

Do not let them pick you up, or volunteer to pick them up. Meet them there, and make sure you have your own transportation. And learn from me, it is better, even if you go to a second location, to follow them there (ask for the address to GPS it so you can check it out first) rather than riding together.

When the date is ending, keep things light. Even if the date was not successful, thank them for their time, follow up with a text or email thank you, and don’t lead them on. If the date was great, that’s awesome – but still don’t go home together that first night. It’s just better for everyone if you leave them wanting more than find out you wanted less later.

Step 5: The After Math
After the date was over, assess the situation. Are they a good fit for what you are looking for? Could you see it going somewhere positive? If the first date was awkward but you liked them, consider giving them a second chance. A lot of people put so much stock in to the first date that everyone gets nervous and it can be downright clunky. But the second time around, you both know what each other looks like and can be more relaxed, and that is often a better gauge of what is going on.

If it’s obvious to you that this is not a good fit, but the other person doesn’t get it, be nice but honest. Briefly honest. You don’t need to go in to a droning lecture ad nauseum about everything that you feel doesn’t work – it’s not healthy for anyone. Just thank them and let them know the truth: “I enjoyed [xyz] but I’m not sure this is a good fit for me. Thanks so much for your willingness to meet me – I hope you find what you are looking for!” And then move on.

Keep the Dalton rule of thumb. . . Be nice. Until you have to stop being nice. Then be firm but polite. (I love Roadhouse!)

If you think it was great but they don’t seem to think so, still be nice. They are entitled to their own opinions, and they are doing you a favor by opting out early. Learn from it, laugh about it when you can, but move on. Each experience is an educational/entertainment opportunity – so use it!

If it’s going well, and you both give the option thumbs up – well then huzzah! Carry on!

This information was shared for anecdotal purposes only. Your actual results may vary.

Walks on the Beach

True online OKCupid encounter* commences now (I even left in the typos):

He:  How are you?  If you were walking on the beach and saw someone laying there buried in the sand, completely, with only the face barely peeking through, just enough to breathe, would you step on their face or walk around?  Lol.

(long pause)

Me: Umm, is the tide coming in?  And am I barefoot or wearing shoes?  Cause they might bite.

He:  Well tides low probably and ya might have flip flops on, why? youed step on it? lol.


Me:  Would you?

He:  well Honest, I would try the being buried part face peeking through but I do have alittle trample fetish, so id dare you if it was my face.

Me:  Lol.  I’m not in to trampling that much.  But that’s an interesting conundrum.


He: would you do it?

Me:  Step on your face?  Probably not.

He: yes, and OK, know anyone that would?

*results may not be typical.  Consult with a physician before starting any new dating plan.

I feel I would be remiss if I did not finish this story, even though it may cast a somewhat disparaging light on me.  I did not reply to Trotter’s last email, but within a day or so, I got another one.

“. . . I would still like to meet you for lunch one day, but I don’t want to pressure you.”

To which I replied:

Thanks.  I’m not sure that we would be a good fit – I think we have different mindsets on things.”

He thanked me for my time, complimented me again on my eyes, and went radio silent.  Five days later, I received the following email from him.

“Good morning. I hope U R doing well. Curiousity has gotten the best of me. I know U R not interested in me, but I have to ask. What did I say that made you think we have different mindsets? Was it my comment about not dating outside my own race? If so, I am not racist in any way. I have black friends and black co-workers whom I treat just as I do anyone else, with the respect they deserve.”

(Okay, content aside for a minute.  U R?  Seriously??  You are in your 40s – you can spell it out.)

At first I was just going to ignore his email.  A part of me just wanted to delete it and him from my memory.  But finally, I gave in to my more wicked side. 

I waited two days before answering back:

I apologize for not getting back to you sooner.  Yes, the race comment was a big turn off.  I know you don’t view yourself as racist, and I get that.  But I am part black – and you obviously would have an issue with that.”

Here is where you may judge me, however harshly.  Can I prove that I have any black in my genetic makeup?  No. But I’m French and y’all know that we are lovers, not fighters.  If history has taught us nothing else, it has taught us that we French would lay down for anybody. My family tree is a rainbow of races and creeds. I know I’m multi-racial.  What races?  I don’t really know, nor should it matter.  And that’s my point.

Here’s what Trotter answered back:

“There is no need for you to apologize. I on the other hand, want to sincerely apologize to you if I offended you in any way by my comments. I definitely did not intend to do so. I am definitely not racist/prejudice in any way. Two of my nieces are bi-racial and I love those two girls just as much as I love every other relative I have, and I am proud to be their uncle. As I said before, my step-sister is divorced from my brother-in-law, who is a black man, but they are currently back together, though they are still divorced.

 I currently live with my step-sister, her ex-husband, and my two bi-racial nieces in [redacted]. I have never dated anyone outside my race, and I have chosen not to do so up to this point based solely on how some of our dumb ass family members view bi-racial marriages. I have witnessed my step-sister being treated differently by some of our family members due to her previous marriage and her two youngest children and it really angers and frustrates me. I hold NOTHING against you for being bi-racial. I base my opinion of you based solely on you, not your race, skin pigment, education, etc.

In my opinion you are a pretty, intelligent woman, whom I am still interested in, but I understand my comment turned you off and I REALLY hate that. I have no issue(s) with you being bi-racial, and that would not keep me in any way from wanting to meet you, learning more about you, or date you, but I understand if you choose to not talk to me again. Take care and again I am sorry.”

I appreciate that he apologized.  I appreciate that that he tried to make amends.  He’s still an idiot, but I appreciate what he tried to say.  And that he willingly admitted that he’s not man enough to face his family who may be more racist than he is.

The one statement that really stuck in my craw was this:

“. . . I base my opinion of you based solely on you, not your race, skin pigment, education, etc.. . “

I wanted to ask him why I was afforded such a privilege of stayed judgment, when the black woman who had contacted him originally was not given that same respect.  Since, y’know, he gives the same level of respect to every black person that he gives everyone else.   

I didn’t respond, and I won’t.   I could go on, but I won’t do that either.

Besides, I’ve found something much better.  But that’s another story.

The Whoosh Factor

Sometimes, I’m just not that perceptive.

 “I tried to hit on you last year when we saw each other at the convention,” someone recently told me.

I tried to think back and couldn’t think of a single thing he said to indicate to me that he was interested.  Nothing sprang to mind.  It’s not the first time that’s happened.

I was washing my car one summer’s day at the local car wash.

Don’t I know you?” a man said.

I looked at him – wondering what he was trying to sell him.  “I don’t think so,” I answered.

No, really,” he insisted.  “Your name is Joey, right?”

I looked at him again.  Nothing rang a bell.

You go to UMass Boston, right? I saw you studying in a classroom one day and came in and talked to you.  You were wearing this cute outfit – pink skirt, white blouse – hair all curly. I know that was you.”

Memory bells rang.  I nodded.  That had to have been 6-10 months before.  And now I was dressed in a ratty t-shirt and shorts with my hair in a ponytail.  I couldn’t have looked more different, and yet he recognized me and remembered my name.

He smiled, “I was trying to ask you out that day.”

Whoosh.  That day we talked, I was single.  I had no idea he was doing anything except being friendly – killing time between classes.  Of course, by the time he told me, I was already 4 months in to a relationship with my future ex-husband.  I never saw the guy again.

Even now, as a wiser woman of the world, it’s Whoosh Central around here. Maybe it’s not really my fault.  I think as a whole, we single people are so afraid of rejection that we never just come out and say what we want to until we have tested the waters 27 times.  

For me, sometimes, in addition to the fear of rejection, it’s because I don’t want to hurt someone else or make them uncomfortable.   So I compliment them, and then compliment other people around them.  I try not to be too overt in my attentions. I’m friendly and flirty all the time. This way, it’s not that I’m necessarily hitting on someone – I’m just that way with everyone.

I have a question to ask you, “a friend asked me one time.  “Before you started dating [last boyfriend], if I had asked you out, would you have said yes?”

Whoosh. I tell him yes.  What seemed obvious to me was evidently subtle to him. Too scared of being pushy, my attentions didn’t even register on his Richter scale until it was too late for him to react.

For all my talk and bravado in public and online, I’m scared to death that if I tell someone that I like them, they will run screaming in to the night. It’s one thing if it’s someone on an online dating site.  So very different if it’s someone I met in the real world.  And there’s the rub.

How can I fuss at potential suitors, when I’m just as bad as they are? Why should I be afraid to reach out to someone I know and say, “Hey – I think you are as cute as heck.  Want to grab a drink sometime?”

Whoosh. I’m sitting here now, feeling like I’ve had the wind knocked out of me.   It was time to stop being afraid. Now the wait begins.

The Tale of Bra Boy

He found me on Yahoo.  I was in the process of separating from my husband and moving to Denver, he lived in Colorado Springs.  He assured me it was fairly close by.   We chatted back and forth over several weeks.   

When I first arrived in Denver, I knew no one other than my landlord/roommate and we didn’t seem to click very well. The internet was my lifeline to family and friends, and he was someone who was close by when others were far away.   Maybe it was the high altitude combined with the glass of wine, but I found myself agreeing to a date.  It would be the First After since my separation.

We talked about our date – he would plan it – I just need to come dressed and ready.  I was trying to figure out what to wear – he recommended, among other things, my red bra. I agreed.

When the day came, I dressed carefully – not too dressy, not too casual.  Took extra time to primp and do all those “extras” you only do for a date or a doctor’s visit. His car was in the shop, so I drove 90 minutes to where he lived. When I first arrived, it looked like the courtyard of Melrose Place.  Upon closer inspection, perhaps Melrose Place if it became Section 8 housing.  But I had driven all this way so I persevered and knocked on the door. 

He was shorter than I pictured, disheveled, in a sweatshirt and jeans – a ball cap crammed on his head. 

“I just woke up,” he said. “Give me a second.”

I stood in the doorway and watched as he shuffled through some papers.  Wait, not papers.  Coupons. 

“Which do you prefer?” he asked.  “Chinese buffet or pizza?”

Since the Chinese buffet was evidently 2 for 1, we decided to do that.  If you are going to go first class, better go all the way.  The plans for after dinner were just as carefully thought out – so we ended up going back to his place to watch a DVD.   He pulled up his sweatshirt and asked me to scratch his back.  Hrmm.  Well, I wanted to see how the movie ended, so I did.  I thought maybe it was a move, but he thanked me and pulled his shirt back down.  He didn’t offer to return the favor.  We sat very chastely on his couch and watched William Dafoe act crazy on screen.

When the movie ended, he turned to me and asked. “So can I see your bra?”

I laughed in surprise. “Is that your move?”

I’m 36,” he said.  “I don’t have time for moves.”

“You’re 36,” I countered.  “You better make time.”

I’d love to tell you that I got up and left Section 8 of Melrose Place with my head held high and my dignity intact.  But it was my First After, I’d driven a long way and worked up a lot of nerve to get that far. And I had worn my red bra. But let’s pretend I did.  Deal?  Thanks.

Let’s just say that sometimes the best part of a First After is that you have nowhere to go but up.

Its Up Two U

I rewrote my dating profile this weekend after a male friend who was on the same site took a look at it for me. 

“You need to sell yourself more,”  he said. “You need to forget about being humble and just put out the best things about you and stick by them.”

It’s hard.  I was not raised to say, “HEY I’M AWESOME – YOU SHOULD TOTALLY DATE ME!” 

These profiles can make you feel like a used car salesman.  So for fun, I wrote up this profile and posted it on Facebook for my friends:

1970s model with a few miles, fairly dependable, good for local travel as well as long distance, fairly low maintenance, comfortable upholstery with no major structural damage. Known to turn a few heads, fairly roomy. Too valuable to sell just for parts.

It took the better part of a day to rewrite everything.  My male friend (and fellow online dater) said it was quite an improvement, and that made me glad.  I even added a special comment to the “You Should Contact Me If” section:

Please don’t message me if:

  • You think “how r u” is an acceptable form of communication
  • You think Hannibal Lecter was a cool role model
  • You haven’t taken a bath since last spring
  • You haven’t had a job in 6 years and need a sugar momma
  • Or you are looking for a green card sponsor

I still ended up with this email from someone:

“well hi i see u stop by would u love two chat i must say that u are a gd looking lady i like what i see so lets chat love its all up two u.”

I replied with:

Thanks for contacting me – but I don’t think we would be a good match.  I wish you much success in your search!

He responded:

Why say that love

To which I typed:

Did you read my profile at all? I just don’t think we are on the same communication level.  But I wish you happiness!

He countered intelligently with:

I am not from over over and nother country okay i am from the states okay

A part of me just wanted to reply with:

Who let you near a computer and told this was how you find women? Truly, you need to rely on buying someone lots and lots of liquor and go that route, my friend.  Or tell them that you are an illiterate deaf mute.  Cause that would totally work better for you than trying your typing skills to woo someone.

But I didn’t.  I just didn’t reply at all.