First Date Winners: 10 Surefire Tips for Dudes Who Suck at Dating

First Date Winners: 10 Surefire Tips for Dudes Who Suck at Dating

First Date Fears: 

We’ve all had them — those first date doubts that make palms sweaty and heartbeats rise. 

What if you come off as boring? Or can’t think of anything to talk about? Or the evening you planned is all wrong? And maybe you’ll say something stupid at the end of the date to ruin it. 

Or…how about this scenario instead, Dude: I set you up with a surefire plan for a great first date that makes you look confident, conversive, charming, and downright likeable? Sounds much better, right?

When you’re feeling calm about the details, you can actually relax on a first date and enjoy yourself. This will make you all the more attractive as the evening progresses. 

And this isn’t just optimistic guy talk. I’ve workshopped all the below tips with women to make sure I have it right. Follow this advice and you’ll be a dating superstar in no time. 

Here’s your 10 surefire tips to having a winning first date!

#1: Plan Something to Do!

The week before your big date, come up with a plan for what the two of you can do. Showing up and asking, “So, what do you want to do?” is a major turn off. You want her to feel that you’ve been thinking about the date and put some effort into it.

Do not get too elaborate in your planning. “Keeping it casual” should be your first-date philosophy. You don’t want to set a standard that will be impossible to maintain or makes you look desperate. 

One note of warning — do not make plans where you know your friends will be present. You don’t want her to feel that she’s being auditioned by your buddies. 

Start simple and keep the focus on getting to know each other. A meal at a not-too-loud location is always a safe bet.

Other budget-minded ideas include street fairs, farmers markets, art shows, museum installations, a seasonal/holiday event, or a picnic at the park. 

#2: Reach Out Beforehand

You might be keeping in touch regardless, but be sure to make contact the day of your get-together. Send a text saying you’re looking forward to the date (make sure she knows you’re thinking of it as a “date” and not two friends hanging out) and mention the time you will be meeting.

Offer to pick her up but give the option of meeting at the venue. If the two of you don’t really know each other yet, you want her to feel safe.

Keep your pre-date communication short and sweet so that you’ll some details and topics to talk about when sitting together.

You want her to know you’re thinking about her, but still leave enough mystery that she is anxious to fill in the blanks.

#3: Double Check Your Appearance Before Leaving

Do I even need to mention that you need to shower and brush your teeth as part of your date preparation? That should be a given.

As for your attire, stick with the “keep it casual” philosophy. Jeans or shorts might be okay, depending on where you’re going. But a nice shirt with a collar is always appropriate.

Absolutely leave the gym clothes at home! Trust me on this one — saying, “I just came from the fitness center,” will not impress her. If you are in great shape, don’t worry, she’ll figure it out other ways.

#4: Make the Right First Impression

When you first see her, make direct eye contact, give her your best smile, and compliment her appearance. DO NOT come off like a dating rookie and say she looks sexy or hot. Furthermore, do not appear lukewarm by saying she looks nice or fine. “Nice” is what you say to your sister and “fine” implies you don’t really care how she looks. 

So what is a proper greeting? Repeat after me: “Wow, you look wonderful.” Alternatively, you could say great, terrific, or amazing. Simple and effective.

Another first-impresssion tip is to be sure to open doors for her all evening. Also hold doors open for others coming just before or after. It’s just good manners. 

#5: Make the Conversation Mostly About Her

I have had many women compliment me on being a great conversationalist. What’s my secret? I don’t think it’s much of a secret at all — I listen and ask lots of questions about whatever she’s talking about. Pretty simple, huh?

This works especially well of you’re on the shy side and would rather she did more of the talking.

Here are several conversation starters you can memorize ahead of time and drop in anytime you feel an awkward pause might be coming your way:

  • “So how was your day?”
  • “Tell me more about your job.”
  • “How did you come by having the job you’re at?”
  • “Tell me something about where you grew up.”
  • “What other places have you lived?”
  • “Did you grow up with a big family?”
  • “What kinds of hobbies do you enjoy?”
  • “Where have you traveled to so far?”

Notice how all these conversation starters have built-in follow-up questions for you to ask? Within a few hours, you should know copious and intimate details about her background, job, family, and personal interests. 

Do not ask questions just so you can lead the conversation to something you want to tell her about yourself. Keep it mostly about her.

And remember, keeping the focus on her means not being on your phone all night. If you really want to impress her, leave your phone in a pocket. 

By the end of the date, she will feel you are genuinely interested in her life. Yet she will realize later that she still wants to know more about you. 

#6. Offer to Pay the Check

When the check arrives, immediately reach for it and say, “Let me take care of this. I really don’t mind.”

I know it seems antiquated that the man should pay for a date, and personally I think it’s appropriate to share the expenses if you keep seeing each other, but to make the offer on your first date is still the classy thing to do.

If she insists on paying half or at least covering the tip, don’t argue.

#7: Have a Second Destination Ready

If the date just isn’t going well despite all your efforts, you’ll probably want to skip to the next tip and wrap things up. 

But hopefully you’re both having a great time and not ready to say goodbye.  This is when you get to show you’ve got some game when it comes to dating. 

Have a second destination already in mind and say, “I know a great place not far from here I’d love to share with you.” Excellent ideas include coffee shops, ice cream parlors, sweet shops, wine bars, local book stores, or gift shops that carry quirky items.

The real point of the second destination is to give the two of you more time for conversation while you stroll between locations. This is also an excellent opportunity for you to be a gentleman and offer her your arm as you walk. Remember, good manners never  go out of style.

#8: Close Out on a Good Note

Depending on your travel arrangements, offer to accompany her to her car, train station, taxi stand, or front door. Your gesture should be appreciated, but don’t push it if she refuses. You always want her to feel safe with you, and that includes how she wants to say goodbye. 

As for the actual act of saying goodbye, don’t let it get awkward. Just move in for a hug or a kiss on the cheek. If she’s interested in more, she’ll linger and let you know. 

If you already know you’d like to see her again, don’t be afraid to say so. An excellent parting comment is, “I had a wonderful time and hope we can do something else real soon.” This makes your intentions clear without being dramatic or pushy. 

Conversely, if you’re not likely to want a second date, DON’T LIE! Be respectful and simply say, “I had a nice evening, thanks for having dinner with me.” 

Notice how most of my tips center around you just being a basically cool dude? It’s really not rocket science. “Don’t be a jerk” should be your constant dating goal.

#9: Follow Up Within a Day

There’s no hard and fast rule that says when you should follow up after a successful date, but don’t wait more than a day. 

If it takes a while to arrive home after you say goodbye, you might go ahead and send a text right then that says you arrived and will reach out soon about follow-up plans. 

Otherwise, send a message the first half of the next day so she knows you’re a man of your word about making contact and wanting to see her again. 

Stay tuned for an upcoming article about how to impress her on your second date!

#10: Remember to Have Fun!

Most of these tips were centered around making sure your date had a good time and felt well treated by you. But after the date is over you need to reflect on a VERY important question — did YOU have fun with HER?

If you go to the exceptional effort to plan a unique date, make excellent conversation focused on her, offer to cover the check, and treat her like a lady, she really has no reason not to be pleasant and interested company. 

If she’s kind of a dud and doesn’t respond to your best stuff, well Dude, it ain’t about you. She’s just not a match for your personality and you should cut bait after one date and move on to someone you really feel a connection with. 

You’ve now got 10 solid tips in your dating toolbox. You might still have a sweaty palm or two, but you get out there and have some fun being the excellent Dude you are.