Exactly What You Should Do For Your First 5 Dates If You Want A Real Relationship

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Dating, yet another industry millennials are seemingly trying to kill. The only difference, this time it’s on purpose. 

Our generation doesn’t date in as typical a fashion as those before us. We aren’t even meeting people the same way! Sure, people still meet people at bars and through friends of friends, but even online dating has gotten so casual, you’re doing it on while you wait for your train to come. Then suddenly, you finally meet someone! The only trouble is, when you meet people as casually as swiping the same direction on an app, it tends to influence both parties going through the relationship just as casually. 


Be deliberate with your dates. We all have enough friends.

You’ve finally met someone and now you want to get to know him or her better, so you go on dates. That’s nothing new. Except now, with cell phones and social media, we are in constant contact with one another. And with a lax dating culture, you may be seeing each other much more frequently than just on dates.

So, we have devised the best date ideas for dates one through five when you meet someone new.

To clarify, these are not necessarily the first five times you two see each other. “U up?” does not count as a date, and neither does, “I’m just hanging at the house, feel free to come by.” Her going to a show with your friends, and you going to the bar with your friends, and linking up after the show is great! But it is not a date. These are deliberate dates.


Also, we listed five date ideas, but get creative with them, don’t work straight from a list. That guy is a creep.

1. Casual dinner

Don’t psych yourself out. It’s a first date. This should be nice, show the other person you are invested, but not too nice because how many of your last first dates were also the last date?

When you ask your person out, be sure to specify that this is indeed a date. (Especially if you met via friends.) Now that you are on a date, keep the conversation light and the meal just as light. We don’t need you carbo-loading on pasta. You need just enough food to keep you together after the (probably) two drinks you’ll have.

Go somewhere with low lighting but not romantic. We are going for a cool vibe. You need a little bit of a crowd so you have to lean over the table to talk to each other, but not so loud that you are shouting.


RELATED: 5 Amazing First Date Ideas That Are WAY Better Than Dinner And A Movie

2. Post-work drinks

We are all working professionals in big cities. It’s amazing we are finding the time to date at all. We don’t have much free time. Now our weekends are being taken up by dates. Alas, here’s your solution. After work drinks are great. It’s only your second date, so it’s casual enough, and early enough in the evening that you can do it during the week. This isn’t drinks with the coworkers, so be sure to avoid loud bars and their “usual” spot.


Keep it light, margaritas are a good idea, maybe a few craft cocktails. It’s ultimately up to you, but two Bud Light drafts look less like a date and more like you and your partner had to work a tough case. Keep the conversation flowing and don’t black out. (I can’t believe I have to include that reminder.) If that date is going well feel free to roll it into dinner.

3. Day date

“Day Date” what could that possibly mean? This is your first day date. This has all the potential of being super fun but is also tricky. You could just be grabbing a lunch at a sidewalk café or this could turn into a 10-hour adventure where you spend all day together. Prepare for either option.

This is where you get to show your date what kind of things you’re into, and (hopefully) you’ve been paying attention to what they like so you can offer something of their interest.

RELATED: 20 Of The Best Date Ideas That Will Help New Couples Get To Know Each Other Better


This ranges from getting a cappuccino to hitting a bookstore, city walk, museum, lunch, cute ice cream cones, you can do anything. As long as the conversation is flowing and you’re having fun, keep the date going. A brewery before peak hours also has a lot of potential. The only rules are, don’t suggest starting too early (we catch up on sleep on Saturdays) and be flexible. If you have three things planned, that’s great! But if you’re walking and she sees a cool little boutique store, pop in and check it out. Dating is fun. Go with the flow!

4. Brunch

What would a millennial dating list be without brunch? Remember, this is not brunch with your family on Easter. This is a (probably hungover) (probably) boozy brunch. Do not overdress. This is where you will each be looking your most vulnerable. It will probably be the earliest you have seen each other, and you both may have had a late night.


Girls, throw the hair into an up-do, guys hats and sunglass are okay here. If it’s the winter, wear your chunkiest sweater. This is your fourth date, but you’ve probably hung out much more than that. You should be somewhat comfortable with each other at this point.

This is a very important date for a few reasons. First, you’re going to find out if they are a mimosa or Bloody Mary person. And more importantly, there’s a good chance this is where you meet her friends.

By the way, she’s allowed to have friends there and you are not. Her friends already know all about you anyway. You know each other well, but it’s still the fourth date, you aren’t setting friends up yet. Besides, your friends will ruin it, because they think that’s funny, and if you’re agreeing to this date, I hate to break it to you, but you like this girl.


5. Romantic dinner

Here’s where we pull out all the stops. Pick a nice restaurant. Let her know that it’s a nice place and to dress up. She’ll appreciate the heads up. You also have to dress nice. Put the jeans away just for tonight. Are flowers over the top? Probably, but they fit right in tonight. (And are too often neglected).

Tonight is where you get promoted from her Instagram stories to her Instagram post. It’s special. Call ahead and make a reservation, ask for a nice table. Tell them it’s for an occasion and they will be happy to oblige. She is in her best dress and a great set of heels, you have a suit on, walk in oozing confidence and people will think you do this every weekend. It’s fun. Once you’re at the table split a bottle of wine and talk about what is on your mind. You know each other at this point; conversation should be easy.

And there you have it. You’ve been on five dates with someone you like. You’ve probably hung out an additional seven or eight times now. This has probably been going on for a few months. You may even be considering calling this person your significant oth—okay I’ll pump the breaks.

What you do with this list is ultimately up to you, remember to get creative, and ultimately make sure you both are enjoying yourselves. If it doesn’t work out, that’s okay, but best of luck to you anyway.


RELATED: This Is How Many Dates It Takes To See If Your Man Is Really Serious About You

Emmett DeLaney is a Boston based stand up comedian and writer. More of his work is available on his website. Follow him on Instagram.