fifteen medium hairstyles for a first date

Medium

15 medium hairstyles perfect for a first date

By Ava Diaz

Published: 13 Feb 2025

First dates. Ugh, right? The butterflies, the awkward silences, the pressure to make a perfect impression. And let's not forget the hair! I remember one disastrous first date – I'd spent hours on a complicated updo that ended up looking like a bird's nest by the time we'd finished appetizers. Lesson learned: Keep it simple, chic, and most importantly, you. This post is all about medium-length hairstyles that’ll make you feel confident and gorgeous, no matter what the date brings. So ditch the hairspray-induced helmet and read on!
woman smiling confidently with medium length hair on a first date

woman smiling confidently with medium length hair on a first date | Image: Supplied

Effortless Waves

This is my go-to. It’s romantic, flirty, and takes about five minutes to style. Just use a large-barrel curling iron or even some texturizing spray for naturally wavy hair. You can also add a cute headband – this elevates the look without feeling overdone. Think effortless beach waves, but make it a date night. Plus, it looks great with almost every outfit, and who doesn't love versatility?

Pro-tip: A little bit of shine serum can add that extra touch of glamour without weighing it down.

woman with medium length wavy hair

woman with medium length wavy hair | Image: Supplied

Sleek and Straight

For a modern and sophisticated vibe, a sleek, straight hairstyle can't be beat. This look screams confidence and polished sophistication. If you have naturally straight hair, great! Just add a heat protectant and go. For those who like to use a flat iron or hair straightener, make sure you're not using too high of a temperature to avoid damaging your hair. A quick blast of shine spray finishes the look, giving that sleek and smooth finish that's perfect for a romantic dinner.

woman with medium length sleek straight hair

woman with medium length sleek straight hair | Image: Supplied

The Classic Low Bun

Simple, elegant, and undeniably chic. The low bun is a timeless choice for a first date – it's polished yet understated. A low bun works great on both fine and thicker hair. For extra style points, add some bobby pins with embellishments or a delicate hair clip. Keep it clean and neatly tied for a formal feel, or loosen a few strands for a messier, more relaxed style.

woman with a low bun medium length hair

woman with a low bun medium length hair | Image: Supplied

Half-Up Half-Down

This versatile style is perfect for showing off your hair's natural texture, whether you have curls, waves, or just some volume. It's playful, fun and keeps your hair out of your face while still allowing you to show off its gorgeousness. To get that voluminous look, use a volumizing mousse or spray before styling. You can also add a braid to one side for an additional, beautiful touch!

woman with half-up half-down hairstyle

woman with half-up half-down hairstyle | Image: Supplied

Braids, Braids, Braids!

A side braid, a fishtail braid, a Dutch braid – the possibilities are endless! Braids are so versatile, effortlessly stylish, and practical, too! They are incredibly versatile and make a great look for either a casual or more formal date. My personal favorite is the loose, romantic braid – it’s easy to style and looks beautiful. Just make sure to not braid it too tightly, you don't want a headache on your date!

woman with a braid in her medium length hair

woman with a braid in her medium length hair | Image: Supplied

Messy Top Knot

This is my go-to for a casual, carefree vibe. Perfect if you're meeting for a coffee or a walk in the park. It's effortless, cool and can make you look effortlessly chic. It works well with all hair types and takes mere minutes to style! Just pull your hair up into a high bun, leaving a few loose strands for a relaxed look. A texturizing spray adds volume and texture, even on fine hair.

woman with a messy top knot hairstyle

woman with a messy top knot hairstyle | Image: Supplied

Side-Parted Waves

This is a classic style that never goes out of fashion. A deep side part adds a touch of drama and elegance. The soft waves add a touch of romance, this hairstyle is perfect for a romantic dinner or a night out. You can customize this to your preference by using different curling irons or hair rollers. Try different wave patterns to discover what works best for you and your hair.

woman with side parted wavy medium length hair

woman with side parted wavy medium length hair | Image: Supplied

Accessorize!

Don't underestimate the power of hair accessories! A pretty barrette, a sparkly headband, or a delicate hair clip can transform a simple hairstyle into something special. Just make sure the accessories you use complement your outfit and your personal style, not overshadowing it.

woman with medium length hair with hair accessories

woman with medium length hair with hair accessories | Image: Supplied

Textured Bob

A textured bob is a modern and stylish choice that works well on various hair types. This chic hairstyle is easy to maintain, effortlessly stylish, and requires minimum styling. Just a little bit of styling product to keep those ends looking perfect, and you're good to go!

woman with a textured bob

woman with a textured bob | Image: Supplied

Long Layers

Long layers add movement and volume to your hair, creating a cascade of texture and dimension. It frames the face beautifully and it’s surprisingly versatile. It's a great choice if you're looking for a hairstyle that looks great both up and down. Consider adding some subtle highlights to really bring out the dimension.

woman with medium length hair with long layers

woman with medium length hair with long layers | Image: Supplied

Asymmetrical Cut

Looking for something edgy and unique? An asymmetrical cut adds a touch of playfulness and unexpected flair. It can be styled in many ways, from sleek and straight to tousled and wavy. This look is perfect for those who love to make a statement.

woman with asymmetrical medium length haircut

woman with asymmetrical medium length haircut | Image: Supplied

Headbands and Scarves

Quick, easy and fashionable! Headbands and scarves add a fun, playful touch to any medium-length hairstyle. It can instantly change your look, and it’s great for adding style and personality! Choose something that complements your outfit and personality. So much fun!

woman with a headband or scarf in her medium length hair

woman with a headband or scarf in her medium length hair | Image: Supplied

So there you have it – fifteen medium hairstyles perfect for a first date (or any date, really!). Remember, the most important thing is to choose a style that makes you feel confident and comfortable. What are your go-to first-date hairstyles? Let me know in the comments!

The best hairstyle is the one that makes you feel most confident and beautiful.

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