What are men looking for on a First Date?
The other day, I was lured into a conversation about what men and women find attractive in the opposite sex. As a result, I was asked to write a bit about what I guy might be looking for in a girl on their first date.
As you might imagine, I could probably fill this blog every day for the rest of my life and I still couldn’t explain it all. So I thought I’d share a couple of thoughts that might be helpful to those women who might still be uncertain. Since I’m a guy, I’ll start with appearance.
Be yourself on your best day. If you have straight hair, don’t make it curly. If you don’t usually wear a lot of makeup, don’t make an exception for this date. If you like to wear sneakers wear them. Look your best, but be yourself.
It’s a very honest and authentic way to represent you. Any sort of chameleon behaviors will get sorted out in a short time anyway, so why waste anyone’s time.
Be interested, not interesting. This is the cardinal rule of being a good conversationalist. Like a successful talk show host, ask questions, try to learn about them. Most men LOVE to talk about themselves, and ladies successful in attracting men encourage them. It feeds their ego, gives you more information about your date, and you’ll come across as more interesting to them.
When that check comes, offer to pay. I’m not saying you should pay. I’m just saying that you should offer. His response will tell you a bit about him as well. Hopefully, he will insist on paying.
After the movie or after dinner, when you stop for ice cream, coffee or another drink, pick up that one. This will show him that you are independent. And that’s a good thing.
Lastly, relax, make good eye contact, stay off your phone, and most importantly, enjoy the experience even if he’s not your prince charming.
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The author, Steve, is a 40 year old successful Entrepreneur who lives in the northeast with his wife of seven years and two beautiful children. Steve is an amateur Triathlete who also believes he has a fantastic sense of humor, although this last part is still up for public debate.


Agreed. There’s nothing worse than someone pretending to be something or someone they’re not. Being yourself is extremely important.
Christopher – It can be disconcerting when you’ve gone on several dates with someone thinking you know who they are and what they like, only to find they’ve been pretending so you continue to date them.
When I was single I always offered to pay for something. I never thought the guy should accept (especially if he asked me out), but I always at least offered.
I always try to be myself on dates. I usually prefer to go somewhere nice but comfortable.
As far as being able to tell a lot about someone if you offer to pay, one time a guy took me up on my offer to pay for half the dinner.
I never saw him again…it just showed me he wasn’t that serious about impressing me. I thought it was about the same if I’d shown up in sweatpants.
I was a little put off by #3, “When the check comes, offer to pay,” until I got to “His response will tell you a bit about him as well.” Excellent point. And I think JackieK is right – a man allowing a woman to pay on a first date, especially if he asked her out, shows he doesn’t care about impressing her.
Great post, Steve!
I liked that advice: be interested, not interesting. I had a different idea until now!
This is an interesting post. I think on a first date I am looking for a woman who can:
Hold a conversation.
Get the “Joke”.
Have at least TWO interesting life stories.
Tell me about her life goals/passions.
Have a sense of humor (Important when getting the JOKE)
Offer to pay (AND MEAN IT)
I can tell when a woman wants to REALLY pay for dinner. I can tell the ruse from the real. It’s 2009 ladies and the whole men should pay for everything is really lame. I would never allow a woman to pay, but I know when you mean it and when you don’t. I have never really dated women who have been in better financial situations as I. If I did I would be a lot more willing to allow them to pay.