I’ve written a few times here about how much smart dating strategy is like successful job search.
If you’re wise, you’ll do the same kind of soul-searching initial work for dating that you would if you were job-hunting.
After doing the digging-deep work and setting up your online dating profiles, the next step is to actually go on dates, which correlates to going on job interviews in job search.
Unless you’re very, very lucky and meet “the one” quickly, you’ll be doing a lot of dating.
And that’s okay. It’s good practice to go on lots of dates. It helps you get better at reading people and knowing who will or won’t be good for you.
Try not to set your hopes too high with each new date. Just think of it as getting to know another human being a little bit.
Here are some things to plan for and think about, as you go on first dates, second dates and beyond. If you’ve ever been involved in the job interviewing process, all of this will sound familiar.
Setting Up the First Date
Communicate a little for, say a week or two, before meeting in person.
Email back and forth a few times, and then have a few phone calls to get to know each other a little. One of the reasons NOT to move immediately to a first date – you may be able to weed out some men and avoid at least some dreaded first dates, which are always inherently stressful.
Reserve texting for very short messages.
It’s up to you whether texting is okay. I never liked texting at this point, and for what will probably be longish messages. Texting is better left for very brief or last minute messages.
Determine where to meet.
I always felt a coffee date during the day or something similar is best. If things don’t work out, you’re not stuck waiting for a meal to end. But if everything is groovy, you can linger. I had a disastrous first date, made worse because I let him convince me to meet at a romantic restaurant.
Wherever you decide to meet, pick somewhere you’ve been before so you’ll be comfortable and know where everything is.
Play it safe.
Don’t let a man talk you into letting him pick you up at your house, or don’t suggest that he does. Unless you know him, he is a stranger. You shouldn’t let him know where you live yet. You shouldn’t get into a car with him yet.
You don’t have to go on a date with them.
Even after communicating by email, text and phone for a time, you’re not committed to going on a date with him. If he already shows signs of one or more of your deal breakers, think twice before making a date. First dates are stressful enough. Why put yourself through it with someone who, more than likely, isn’t right for you?
Preparing For the Actual Date
Plan to wear something comfortable.
I usually wore attractive sweaters or knit tops and nicely-fitting jeans on the first date. No fuss deciding what to wear. Nothing to come untucked or be adjusted when I stood up. I was very comfortable sitting for hours, if things went well. If there’s any chance you’ll be doing some walking, wear sensible shoes.
Be mindful of your personal hygiene.
I remember a date with a man whose breath was horrific. I couldn’t believe he wasn’t aware of how bad it was. Be kind. Pop a mint right before your date, no matter how good you think your breath is.
This may be obvious, but wash up before you go. Make sure your clothes don’t smell bad. Don’t overdo it with perfume or makeup.
Prepare some questions to ask him and topics to discuss.
Research him by reviewing his online profile again, Googling “his name” (get his full name as early in the game as you can), or asking the person who referred him to you.
Think about what you want to get across about yourself.
Prepare to answer the typical questions he may ask: “Tell me about yourself”, “What kinds of things do you like to do”, “What hobbies do you have?”, “What’s your favorite movie?”
You may want to write all this stuff down, but then put it to memory before going on the date. I had a first date where the guy actually pulled out a long list of questions he wanted to ask me and began running through them. Things quickly got awkward and uncomfortable. The weird thing was, we were having a perfectly fine conversation without his list.
Navigating a Successful First Date
Be on your best behavior.
Always be courteous and polite. Don’t hog the conversation. Be a good listener and maintain eye contact, but don’t let a gasbag take advantage of that. Keep things positive and upbeat.
An article on OurTime.com (where Cosmo and I met) lists 5 Topics to Avoid on a First Date:
1. Your past relationship / marriage.
While this is a fine – and necessary – topic once you’re more intimately acquainted, your date should feel like he or she is the focus of your evening – not the ghost of a past relationship.
2. Problems with kids and family.
Again, this is too much, too soon. Complaining about relatives (even when warranted) can make you seem critical and stodgy on a first date. Let your partner get to know you better before unloading familial drama.
3. People unfamiliar to your date.
This is probably good advice for any conversation: Limit discussion of unknown third parties to a few minutes or less. Obviously, there are exceptions to the rule (funny stories, relevant anecdotes, celebrities, etc.), but by and large, people aren’t interested in people they don’t know
4. Political and religious viewpoints.
This should be self-explanatory. It’s just rude to pull out the soapbox in front of someone you just met. Your date can’t disagree with you without being “disagreeable.” Politics and religion are very important discussions to have… later.
Talking about finances – both positively and negatively – is very off-putting to most people. And never, ever, complain about the cost of the date if you’re the one paying. It makes the other person feel like you regret taking them out.
Walk in with a big smile on your face.
This works wonders, for both of you. Smiling will help ease your nerves and make you look more attractive, and it will instantly give him a good feeling about you.
Break the ice.
You’re both probably nervous. Think of something brief to say that will put you both at ease.
Who should pay for the first date?
This is something to decide ahead of time. There’s no right or wrong answer. Some women expect the man to pay for at least the first date . . . some expect him to always pay.
I think it’s wise for the man to offer to pay, but I always suggested we split it.
Should you kiss on the lips?
I never wanted the guy to kiss me on the first date (not even Cosmo and I was pretty sure he was “the one” right away), but I would always initiate a hello hug and goodbye hug. I thinks it’s a risk for either one of you to do something as intimate as kissing on the lips. Why take the chance it may turn them off?
Take it in stride if it doesn’t work out.
Don’t put too much weight on the first date. Try not to be crushingly disappointed if things don’t work out . . . it’s just one date. If you really like him, but he clearly doesn’t feel the same about you, it would never work out anyway. Things have to be right for both of you.
Following Up After the Date
Make mental or, better yet, written notes.
What did you like and NOT like about him? Did it seem like he liked you? Do you want a second date with him?
Get in touch the next day to thank him.
Send him a quick text (if you feel texting is okay) or email thanking him for a nice time . . . whether or not you want a second date with them.
If you don’t want a second date, also say in your text or email something innocuous like “Although I enjoyed meeting you, I don’t think we’re right for each other. I hope you find the right one for you soon.”
If you DO want a second date, thank him for the date and say something like “I’d like to see you again, if you’re interested”.
For the first several dates with a man, or maybe always, send a quick text or email “Thank you” afterwards. It’s just common courtesy and he’ll make note of that.
Second and Third Dates . . . and Beyond
Keep your options open.
Even if things are going great with someone, don’t put all your eggs in one basket. Keep dating others, and be open about it if asked, until you’re ready to make a commitment to just one man.
When to discuss various thorny issues.
If you have issues that will impact your potential relationship (health problems, addictions past or present, family commitments, lifestyle preferences, etc.), tell him about them within the first few dates . . . probably not the first date, but the second or third.
If these things are deal breakers for him, it’s better to get them out in the open, and save both of you from being hurt or getting your hopes up.
Likewise, ask him if he has any similar issues.
When should you have sex for the first time?
This is entirely up to you. I suggest you put a lot of thought into this well before you meet anyone, and stick to your plan.
I thinks it’s a colossal mistake to have sex on the first date, but even on the first several dates is way too soon. Don’t risk letting sex muck up what could be the perfect relationship for you.
It’s much safer and wiser to wait until you have a committed, monogamous relationship, and everything about the relationship feels right. Wait until you know that you love him. Trust me, the sex will be better because it will come from love.
Discuss when to have sex with him – including each of you getting a full range of tests for STDs – and come to an agreement about when you’ll take that big step. The discussion itself will bring you closer. If the discussion causes friction, he may not be someone capable of, or ready for, a mature, exclusive relationship.
Don’t overlook your deal breakers.
You should have a list of big things you can’t accept him doing or being. These things will be particular to you. It should be a short list. If you have an extensive list, you may be too picky and you may never find someone.
If you don’t hold fast to your values, you’ll come to regret it. I can almost guarantee it. For instance, if you decided beforehand that you can’t be with a smoker, but he’s oh-so-wonderful and he smokes, and you can’t give him up, you’re probably making a big mistake.