A man and a woman sitting inside a coffee shop looking unhappy.

No matter your Enneagram type, you know exactly how difficult dating can be if you’re single. From ghosting to app fatigue, finding "the one" can be a hellscape of putting yourself out there and getting little in return.

But as an Enneagram Four, your dating struggles may be a little different from others. You’re romantic and idealistic, yes—but you also have trust issues. And that creates a vicious cycle where you're constantly seeking deep connections while simultaneously pushing people away.

If this sounds all too familiar, don't worry—you're not alone. Here are six dating struggles you’ll definitely relate to as an Enneagram Four.

1. Your emotions come off as overwhelming

Type Fours feel emotions deeply. You seek a deep connection when you go on dates, right from the get-go. The catch? Not everyone is as self-aware and expressive of their emotions as you are. Your date may be used to playing it cool as they test the relationship waters. It might be overwhelming for them to see you express a range of emotions so deeply and immediately.

What you can do: Although it’s good to be so in tune with your feelings, it’s a wise move to keep them under wraps until you know someone better. Practice sharing smaller bits of information at a time instead of overwhelming your date with all your thoughts and feelings in one go.

2. You ignore first-date red flags 

When you choose your heart over your head, you may ignore some red flags from the person you’re on a date with as you try to make the fairytale romance you want come true. This is dangerous. It leaves you vulnerable and exposed to the wrong person who may take advantage of your idealism. 

What you can do: Although your heart’s thumping and you have butterflies, invite your head to the great date you’re on! Pay attention to the person’s words and body language to see if any red flags would be deal breakers for you. These are important to notice before you get in over your head. 

3. You ignore others by retreating into your thoughts 

Type Fours daydream a lot. When you’re dating someone, you might confuse your partner by withdrawing into your inner world. You might not be aware that you’re doing this, but suddenly you’ve made the other person feel like you’re ignoring them. They might feel insulted, which can cause conflict or misunderstandings. 

What you can do: Communication with the other person is key. There’s nothing wrong with wanting to escape into your inner world, but it’s good to tell your partner how much you value time and space to think so they know what to expect. Also, think about going on activity dates. Dancing, hiking or going to an art exhibit together will help get you out of your head.  

4. Surface connections turn you off 

As a Four, you always search for what’s missing in your life and relationships. You want to connect deeply with someone, but sometimes it doesn't feel easy because many singles in the dating game are looking for flings or one-night stands. This can leave you feeling quite jaded and cynical about finding the love you want. The result is you expect to be rejected before it even happens. Be honest—are you entering dating apps and meeting new people with your defenses already up?

What you can do: Try to love yourself before finding a romantic partner. Realize that you’re worthy and lovable, as you need to validate this within yourself before you try to find it from other people. Then, be curious about getting to know someone instead of rushing ahead and looking for a connection. Mindfulness can help you to remain in the present.

5. People don’t understand your melancholy 

Fours can be seen moody at times. If people you’re dating don’t know how to deal with your melancholy, they might walk away before giving you a chance. This feeds into your sense that others will never see the real you and you’re misunderstood. As a Four, you have a strong fear of abandonment, but are you pushing people away and turning rejection into a self-fulfilling prophecy? 

What you can do: On a practical level, instead of letting your feelings consume those early dates, try to channel them into creative outlets. Writing, painting or playing an instrument can be therapeutic and help you express your emotions in a productive way. Also, communicate openly with your partner about your melancholic tendencies to eliminate confusion. If you want them to give you a bit of space or if you want to talk about what’s on your mind, ask for what you need. 

6. Resisting group dates because they’re stressful 

When you meet someone new online or in real life, your tendency is to build a one-on-one connection with them. Group dates can be stressful for you, because meeting lots of new people at once is overwhelming and having to make small talk with strangers feels meaningless. 

What you can do: Take control and offer to plan those early dates so you can create that one-on-one experience. If a date pushes back, tell them you’d prefer it to be just the two of you so you can talk to each other and connect. You could offer to meet their friends at a later stage when you feel more confident in the partnership that’s forming.

Final thoughts 

If you’re an Enneagram Type Four, you probably feel stressed out in the dating game. That’s because you’re seeking a meaningful connection and it’s a challenge to find someone who is as all-in as you are. The struggle is real! 

To get through those early dating  moments, try to stay present and pace yourself. No one is saying you cannot be your usual quirky self, but it does help to be more aware of how you’re coming across to your date. It’s important to remember that finding the right person is all about timing and being patient with yourself and others in the process. Another common thread is to communicate about what you need, but make sure you do this when you’ve formed an emotional bond with someone who has shown you they’re interested, so you’re both on the same page. Good luck out there!

Giulia Thompson

Giulia Thompson is an Italian-South African freelance writer and editor with several years of experience in print and online media. She lives in a small town in South Africa with her husband and three cats. She loves reading, writing, and watching thrillers. As an Enneagram Type 4, she’s creative and loves surrounding herself with beauty.