The 7 Most Frustrating Types You’ll Meet on Dating Sites

So, whether you are single because you haven’t yet found a person worthy enough to make you not single, single because you’re divorced, or single because you are widowed, like me – maybe you are considering going on these dating sites also. I suggest that you read this list first, and then have fun, but proceed with extreme caution. And if you are someone who has already been on these sites, then none of what I’m about to write below will be much of a surprise to you, but it might give you a good chuckle or you might relate to every single one of these. So here we go. These are the Top 5 most frustrating types of guys I’ve met on dating sites (and yes, these dialogues were taken from and based on actual conversations I had with actual men on these sites. Exaggeration is used for comedy purposes, but not as often as you might think. 90% of this is real):


I am guessing this is the most common type of guy that us single women run into on these sites. He starts out somewhat normal (sometimes), and then you are suddenly submerged in a conversation of his extreme forwardness, out of absolutely nowhere. It goes something like this:

Him: Hi there. Your profile picture is really pretty.

Me: Hello. Thank you, that’s really nice.

Him: Here’s my number. I don’t get on the site much, so text or call now. Chat me. Ping me. I’m home if you want to talk right now. What are your hours? Where do you live? Do you want to go out tonight? Move in with me. Marry me. Let’s have babies. Do you like babies? Do you have kids? I have 3. I’m looking for someone to be a mother figure to my kids. Can you cook? Do you like Japanese food? I just ordered some. I’ll save you the spring rolls. It will be our special thing. Call me now, babe. I really think we have a great vibe going here.

(A great vibe? What vibe? All I did was say hello! I don’t even know your damn name!!!)


These are equally as shocking and out of nowhere, and come in various forms of inappropriateness. Here are a few I have experienced along this road of dating site adventure, which usually end with me blocking the person from contacting me further:

Him: Hey sweetie. Your eyes are beautiful. Wow!

Me: Thank you so much. You have a really kind smile.

Him: I’d love to see those eyes looking up at me while you’re giving me head! (BLOCK)

Him: Good afternoon. I read your profile and really liked it. I saw that your husband died. I’m sorry for your loss.

Me: Good afternoon to you, too. It is always a good sign when someone acknowledges my husband’s death. Thank you so much for doing that. Not many do the same.

Him: No problem. Hopefully not out of line here, but did you have life insurance, or do you work? I just don’t wanna get involved with someone who can’t support themselves. Just sayin.’ (Aaaaaand …. BLOCK.)

Him: Good morning. I love your long hair. It’s really gorgeous.

Me: Hi there. Thank you for the compliment. How are you doing today?

Him: I’m fine. But I’ll be a lot better if you tell me that the carpet doesn’t match the drapes, if you know what I mean.

Me: Huh?

Him: I like my women clean-shaven. Bare. Wood floor. No hair down there.

Me: Okay. I got it. Jesus. (BLOCK)

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The 7 Most Frustrating Types You’ll Meet on Dating Sites

About The Author
- is a writer, actor, and stand-up comedian, living in NYC. Her first book: "My Husband Is Not a Rainbow: The Hilariously, Awful Truth About Life, Love, Grief, and Loss", will be released in 2017. Twitter and Instagram is @kelleyiskelley and