The best first dates start with preparation and planning.
Unless you’re very lucky, you’re probably going to have a lot of first dates, and many first-and-only dates.
In my experience, most of us need to be willing to devote a fair amount of time to dating.
Successful dating requires preparation and planning. And it requires setting your deal breakers; the things you will and will NOT accept in a partner.
If you don’t know what kind of person you’re looking for, how will you know her/him when you meet them?
In general, it also involves some calculated risk-taking. Meeting people you don’t know and spending probably at least an hour with them is a bit of a risk.
You’re putting yourself out there and need to be somewhat emotionally vulnerable to make an emotional connection with people who are probably strangers to you.
The risks involved with meeting strangers can be minimized by taking basic precautions, as you’ll see below.
How To Have Great First Dates by Following These 9 Guidelines
1. Don’t make a date with someone who clearly is not right for you.
Do at least some prep work for dating and put together a game plan. Think about and make a list of who the right kind of person is for you. And make a list of who would be all wrong for you.
Relying solely on the old method of introductions from friends and family can prolong your dating time. With such a large pool of people on these sites, looking for someone like you, it just makes sense to be there too.
Whether you’re getting the skinny about your date from someone you know, or from reading their online dating profile, pay close attention to what you learn about your date.
For instance, if you know you won’t be happy long term with someone who smokes (even if they say they’re trying to quit), drinks, or has opposing political views (because politics matter to you), you probably shouldn’t go on a date with them.
Or, if you can see from their dating profile that they’re a very angry person, it may be best to pass on them. I remember several dating profiles written in ALL CAPS, which just screams “angry.
Think about the lifestyle you want to have in your third act. If you enjoy quiet pursuits, you probably won’t get along well with someone who enjoys doing big, loud, brash things.
2. Take the pressure off by having a coffee date or other low-pressure meeting.
Going to a restaurant for a meal for the first date can be tricky.
I did this several times when I was dating, and the date never went well.
Part of the reason could have been that, even though I said I’d rather just go for coffee, they talked me into going for lunch or dinner.
If a date pushes you to do something when you say “no” – even if it’s something seemingly innocent like where to go on the first date – that could be a red flag that they’re not going to respect your wishes in other ways, down the road.
If your first date is lunch or dinner at a restaurant, it can be difficult to bug out if you’re waiting for your food or the check to arrive.
One of the great things about a coffee date first date: if you both want to extend the date, you can easily do so. But if things aren’t going well, you can easily duck out quickly.
My favorite first date place was Panera. You can buy a cup of coffee and sit there for hours.
Another benefit, no matter who pays for the date (you, them or you split it), no one will be out much.
The same applies to just meeting somewhere in public, and chatting for an hour or so. You can easily get up and leave, if you need or want to.
If Covid is still floating around, the latter option may be your best bet. You can keep a distance and keep a mask on, if you want to.
- Visit an art gallery or museum. Art galleries and museums make good first date ideas, because the exhibits give you something to talk about that aren’t your standard first date topics. Plus, it’s a great way to add some culture to your life!
- Volunteer. Spending time and making a difference in the world… win-win! Plus, this is a great way to garner insight into how your date treats people less fortunate than they are… you don’t want to be with someone who doesn’t think other are people worthy of respect.
- Hit up a bookstore. Bookstore dates are great first date ideas because you get to explore books and talk about them. Introduce your date to your favorites and let them do the same. – Just try to pay as much attention to your date as you do the books.
3. Dress for comfort but also attractiveness.
If you’re wearing clothes that are too big or too small, or that shift around and make you fidgety, your mind will be constantly zooming back to your comfort. You won’t be as engaged in the conversation as you should be.
Besides your own discomfort, your fideting could send a signal to your date that you’re uncomfortable with her/him. If things are going well otherwise, you could turn them off.
Put some thought into what you’ll wear, before you leave your home. If you’re wearing something new, try wearing it a bit around the house, sitting down sometimes and walking around.
Same for your shoes. Make sure they’re comfortable. Although you may only be sitting down having coffee for your first date, what if things go well and you continue the date somewhere else? You don’t want to be clunking or tiptoeing around in shoes that don’t let you maneuver well on foot.
If you’re meeting for coffee, there’s no need to dress up. Casual is good, but not too casual, like your around-the-house sweats that have seen better days.
I always wore well-fitting jeans and a knit top on first dates.
On our first date, Cosmo wore tight jeans, a crisp white oxford shirt and a suit jacket. The jacket may have been more dressy than needed for a coffee date, but I’ll sure never forget how put together and handsome he looked. I could tell he put thought into what he would wear. It meant a lot.
4. Don’t go into the date thinking this one may be “the one”.
This may seem counterinteruitive especially if you’re searching for your soulmate.
But that puts an awful lot of pressure on both of you, and can make you misread signals.
Instead, think of first dates as an audition for more dates with that person.
And dates are a learning experience. If you haven’t dated in a while, you get to learn what the dating pool is like. You also learn a lot about yourself, and what you need and want in a partner.
I always thought, “Lighten up. This is just one date. There may be more dates with him; there may not.” And I said to myself:
- Go into it with a positive attitude.
- Relax and enjoy getting to know another human being a little bit.
- Smile and laugh as often as possible.
- If things don’t work out, it’s okay. There will be other dates.
5. Keep your feelings, hurts, and anger about your ex to yourself.
I remember sitting through a lunch with a first date (this was one of the times I got talked into having a meal together). We no sooner sat down than he laid into his ex-wife with such angry passion I became a little afraid of him. Not surprisingly, there was no second date.
That kind of talk can easily escalate into a battle for who had the worse ex, which really serves no purpose. And that kind of talk may indicate that they (or you, if you’re the one dwelling on your ex) are not over the ex. That could be real trouble for you.
It’s tiresome and annoying to be the sounding board for someone’s pent up anger at their ex. Anger has no place on a first date, or the following dates for that matter.
6. Safety always comes first.
Work out your safety mindset, before you go on any dates:
Use your own transportation. Besides avoiding risky behavior by your date, you can leave whenever you want.
Don’t get in a car, or walk in a dark, secluded parking lot with your date, or otherwise put yourself in a potentially compromising position.
Don’t let them come to your home. Meet in a public place for the first few dates.
Arrange with an “emergency buddy” to give you a call during the date to make sure nothing has gone wrong. And this gives you an “out” to easily leave, if you want or need to. Instruct them to call the police if you don’t answer their call. And check in with that buddy when you get home from the date.
Make sure your cellphone is fully charged and that various emergency numbers are easily accessible.
Be careful with alcohol. It may make sense to you to have a few drinks on first dates, to loosen up and have a better time. But alcohol leads to poor decision making. It’s best not to drink at all, or limit it to just one drink.
Keep your purse (for women) and any drinks always within eyesight.
Trust your gut. If something feels wrong about your date, don’t continue with them. If you feel threatened or unsafe because of their behavior, get out of there.
7. Don’t become someone you aren’t.
Something that I think plagues women more than men: We tend to try to meet a man’s requirements for a relationship, even if they go against our nature.
For instance, we may say we like hiking or kayaking or some other sport, when we absolutely do not.
This kind of thing also applies to men, of course. They may put on a different face than who they really are, when they’re on a date.
You probably know the reason this kind of tactic can backfire. Let’s say you succeed in attracting and holding on to the person. Soon enough they’ll find out the truth, unless you plan to pretend for as long as the relationship lasts, that you love the things you don’t love.
8. Watch out for love bombers, catfish, predators, scammers, narcissists, etc.
Unfortunately, you may come across people who are up to no good when you’re dating.
And they can come through people you meet on online dating sites and those that people you know introduce you to, although the latter may be rarer.
My only means of finding dates was the dating sites. A few times I came across men who were probably scammers of some kind or other.
I never met any of them in person because red flags went up from the very beginning and I discounted them.
Some wrote me disjointed emails that didn’t make a lot of sense. They included lots of references to how beautiful I was and overall read like someone for whom English was not the first language. They said things that didn’t really relate to me. I figured they were form letters intended to win me over and then they’d ask me for money.
Have you heard of “love bombers”?
Love bombing is a manipulative dating practice characterized by things like giving expensive gifts, lavish vacations, or excessive flattery. It’s all done to get an upper hand in, and control, the relationship.
Cosmo wrote an in depth article about love bombing and how to avoid becoming a victim.
A few other men I was suspicious of seemed like legitimate people. They gave me their full names and I was able to Google them and find out something about them. But they never wanted to meet in person. I figured they were either married or in a relationship, and were trolling the dating sites on the sly.
I’ve written about how to spot nefarious people like this in my article, Online Dating Advice Every Man and Woman Over 60 Needs To Know.
Besides the people who are out to purposefully do you harm, there are the narcissists, who can be more difficult to identify. They may not be such terrible people, but extreme narcissists are typically not great relationship material.
An overriding character trait is their ability to be utterly charming, and make it seem sincere. Since Narcissistic Personality Disorder (NPD) kicks in during early childhood, they’ve had a lot of practice being charming by the time they reach adulthood and have perfected it, because it serves them so well.
They win us over by making us feel like we’re special. They can be very good at making us feel very good . . . at least for a time.
I was married to such a person for a long, long time, but didn’t realize he was a textbook narcissist until after it all ended. I was totally blind to it, and didn’t really know what it was until I was in therapy after my divorce.
A major red flag presented itself early in my marriage. My husband spent an hour every morning preening in front of first one mirror in the house, then the next, and then the next. If I tried to have a conversation with him when he was gazing at himself, it fell on deaf ears. He seemed not to hear me, or be able to see me, so enrapt was he with his mirror image.
Read more about all this in my article, 9 Signs That You May Be Dating a Narcissist.
Even being cautious, you may still get sucked in by no-good people, like the ones I described above. But be on the lookout so you can avoid getting hurt or taken advantage of, or going too deep into a relationship with one of them.
9. Don’t have sex on the first date.
Even if you fall head-over-heels for someone on the first date, proceed with extreme caution. No matter how great she or he is, or even if all you’re looking for is quick hookups, take it slow. The “sex hormone” oxytocin may be raging within you, causing you to make hasty, unwise decisions . . . like hopping into bed with them way too early.
What’s wrong with having sex on the first date?
Once you have sex, and that oxytocin is raging at least at the beginning, you’re likely to overlook (or not notice) the red flags you should be watching for. And you may set aside the deal breakers you so carefully worked out ahead of time.
You could find yourself several months into a relationship with someone who mistreats you. At that point, it may be very difficult to disengage with them, and they may not be willing to let you go.
And having sex too soon can put you at serious risk for various STDs (sexually transmitted diseases), Covid (if it’s still around when you read this), or even bodily harm from someone who turns out to be physically violent.
If, instead, you set a time period (for Cosmo and me it was a few months), before which you won’t have sex, you have time to get tested for STDs, and to assess whether you’re right for each other.
If you’re looking for your soulmate or lifetime partner, doesn’t it make more sense to make the first time you make love special, instead of responding to hormones and rushing in too fast?
FAQs for the Best First Dates
The first step is to be prepared and plan your dates carefully. Know what you’re looking for in a partner and set your deal breakers.
Yes, online dating sites offer a larger pool of potential partners and can be a valuable tool to meet like-minded individuals.
Do some prep work, create a list of the qualities you seek in a partner, and pay attention to the information you gather about your potential date.
Opt for a coffee date or another easy in-out meeting, as it allows flexibility and a quick exit if needed.
Dress comfortably but also in a way that makes you feel attractive and confident. Avoid clothes that make you fidget to arrange them.
It’s better to approach first dates as an opportunity to get to know someone, not as a search for a soulmate. Keep an open mind and enjoy the experience.
It’s generally best to avoid discussing your past relationships, hurts, or anger about your ex on a first date, as it can create discomfort and unnecessary tension.
Always prioritize safety by using your own transportation, meeting in public places, and having an “emergency buddy” who can check on you during the date.
Be authentic and avoid pretending to be someone you’re not. Pretending can lead to problems later when the truth comes out.
Be aware that some people have ill intentions. Watch for red flags, unusual behavior, and signs of manipulative tactics.
It’s generally best to avoid having sex on the first date, as it can cloud judgment and potentially lead to unhealthy relationships or health risks.
Waiting allows you to assess compatibility, build a connection, and take necessary precautions, such as getting tested for STDs and ensuring your emotional safety.