Online dating is still a fairly new way of finding love, so it’s natural for it to be a little, well, unnatural, at first. Whether it be in person or online, first impressions are still the most important beginning to any kind of relationship. Too often then not a first message can ruin the potential for the whole relationship. ‘Act natural but stand out’ can sometimes be a difficult medium to meet. But no need to worry because HelenMeetsTroy is here to give you some tips in transferring that in-person naturalness online.

1. “What do you enjoy doing in your free time?”

This is your go-to opener of a conversation. One of the most important ways of connecting with someone is finding common interests. By learning about someone’s hobbies, interests, or routines, you can gage the type of person they are. This conversation starter opens their world to you and creates an introduction of where you could possibly fit in!

2. “Have you traveled anywhere interesting lately?”

Travel is extremely important to some people, as it symbolizes perspective, worldliness and adventure. This opener will lead to more questions and discussions like

“My favorite place use to be Rome but this past summer I recently went to Venice and fell in love with it! The cities there are so diverse,”


“Work has kept me pretty busy lately but my brother just traveled to Peru and said it was amazing, so I’m adding it to the top of my bucket list!.”

This conversation starter will reveal a lot about the other person and never lead to a lull in the conversation.

3. “If money were no object and you could quit your job tomorrow, where would you go and what would you do?”

Fun fantasy questions are always interesting to answer. They reveal a person’s hopes, dreams, hobbies, and flirtatious side–perfect for online dating conversation starters. It’s also a more interesting question than other inquiries the person receives from other prospective dates; such as ‘where are you from,’ or ‘why did you decide to sign up for this site?’

4. Asking for Advice

Everyone loves to feel like their opinions are being listened to and taken into consideration–so to show you’re giving someone your undivided attention, you can ask them for advice! For example, if their bio says “Avid hiker” you could say

“I see you enjoying hiking, I’ve tried XYZ trail and loved it, do you recommend any others around here?”

5. Pull something from the profile.

A great first impression is to show you did your research and are interested in the other person’s interests. If their profile says “Big Adele fan,” ask the person if they’ve ever been to one of her concerts. Or if there profile says they’re “Originally from Texas,” you can ask them if they caught the Cowboys game last weekend. You can never go wrong with a conversation opener that address their interests or background.

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