Ask Eileen

Your Go-To Dating Advice Chat

Need Quick, Honest Dating Advice?

Ask Eileen is here to help. Whether you’re crafting the perfect text, navigating awkward date moments, or figuring out if they’re really into you – Ask Eileen is just a message away.

With a warm, no-judgment approach and real-talk advice, Ask Eileen offers smart, supportive guidance tailored to your situation. Think of her as your dating-savvy best friend!

What Can You Ask Eileen?

First Impressions

What should I say in my first message? How to make my profile stand out?

Date Dilemmas

Should I go on a second date? How to handle the bill? Is this a red flag?

Relationship Advice

How to define the relationship? When to introduce them to friends?

How It Works

1. Click Chat Button

Click the “Chat with Eileen” button to start a conversation

2. Ask Your Question

Share your dating situation or question with Eileen

3. Get Expert Advice

Receive personalized, thoughtful advice in real-time

Whether you’re newly single or have been navigating the modern dating landscape for a while, no topic is too small, too weird, or too complicated…just Ask Eileen!