Mother Knows Best: Dating Advice from Mom

Today is maybe the most important day in my life, my Mother’s Birthday.

As her birthday was approaching I couldn’t think of any better gift for her, and my readers, than to interview her about sex and dating. The interview got awkward (for me at least) but I have to admit, she knows a thing or two about dating.

I’ve always asked my mom for dating advice, going back to the 5th grade and I thought you guys would love to hear from the originator of the Tao of Indifference.

 So, without further ado,  here is:

Dating Advice from Mom

1. What is the biggest mistake men make when they’re dating?

Expecting sex after a first date

2. What is the biggest mistake women make when they’re dating?

Expecting lavish outings. Women sometimes want the world on a first date.

The biggest mistake is having unrealistic expectations

3. What’s the worst thing to do on a first date?

Going to the movies, or a concert. Don’t take them to meet family, don’t take them home…unless you’re just hooking up. In which case anything goes

(This was the first answer that made me laugh uncomfortably. Thanks Mom!)

4.Where is the best place to go on a first date?

Parks, museums, not bars unless it’s more of a dinner or dessert bar.

So, don’t go on a date for just drinks?

Never go on a date for just drinks.

You know, I’ve told people before that they should do the opposite, go on a date for just drinks

Why is that?

Well part of it is the cost. Going on a first date can get expensive if you’re doing restaurants.

In that case, dinner should be a compromise. The man should ask the woman what sort of cuisine she wants, after that he does some research on a place they might both enjoy and won’t break the bank.

5. What’s the best way to reject or breakup with someone?

A good way is to say something along the lines of “My life is full right now and I don’t have time to devote to dating you”, or “I want to continue to date other people” if they’ve talked about being committed. Or, you can always say that your lives are going in two different directions.

The lame way to do it is to not call, not text, block them, ignore them, etc.

6. Best advice you would give to someone who has just been rejected or broken up with?

Keep at it. Don’t stop dating. Just go back out there and date. Don’t try for a relationship, just date. You’ll find that it wasn’t your fault that things didn’t work out.


My mother and sister circa ’82 – ’83

7. What was the hardest part of dating as a single mother?

Having to conduct myself in a way that I thought a respectable woman should act in front of young men (editor’s note: My mom has 3 sons and a daughter). There were times where I wasn’t able to go on a date because I knew I couldn’t stay out all hours of the night.

8. What’s the hardest part of dating after a separation or a divorce?

You become more guarded, more sensitive and less flexible in relationships. Your antennae are always up, always on the look out for B.S.

So what advice would you give to someone who has just had a separation or a divorce?

Take it easy, go slow, and have fun

If you’re not having fun, don’t date someone.

This is your opportunity for you to try new things and go on the dates you want to go on. Planning the dates doesn’t always have to be on the other person so now you get to do all the things you wanted to do.

9. Can straight men and women be just friends

YES. Hell yes

10. Best advice for a guy who is wooing a girl?

Pay attention to the small things and let her know you notice.  Compliment her on changes in her appearance. If you do gifts, do something small and meaningful to her

11. What’s the key to a happy relationship?

Be as open as possible with very little restraint on what your willing to do. As a couple, communication is very important and always try to communicate earlier rather than later. Always look to spice things up, whether its clothes, the house, or sex. Most importantly, maintaining your individuality is key. You need to have a separate life from your partner.

12. Should a guy pay for a first date, even if he never wants to see the girl again?

It depends on who initiates the date. If she asks him out, she should pay. If he asks her out, he should pay, even if he isn’t interested.

What if this person is so bad you don’t ever want to see them again?

If the date is that bad, just end it early. If you asked them out, you have to pay.

13. What is the best place to meet someone?

Walking down the street. Walking down  the streets of NYC I’ve met the most interesting people.

14. What do you think of online dating?

It requires a lot of time and energy. The success rate doesn’t seem worth it. It’s for people who have an abundance of time on their hands.

You know it’s funny you say that because I often come across people who say they don’t have the time to meet people normally, that’s why they date online.

Well in that case they might just be looking to hookup, which is different.

15. Would you ever try online dating?

Yes. I have actually, I was on a website called Tagged in 2006. I met some interesting people. In fact, I went on an online date that involved flying to LA. 

Online dating can be fun but it can definitely be time consuming.

Online dating is like going to a sandlot in a park with a sand sifter and trying to find jewels that way. You might find something valuable but you have to sift through A LOT of sand to get there.

16. Do pickup lines work?

They’re corny. You ave to either be really drunk to fall for one, or the person saying it has to be really, REALLY charismatic. Pickup lines are part of conveyor belt conversations

17. Who should initiate a first kiss?

Either person, but my advice is to ask “Is it ok if I kiss you?” because it’s an innocent statement but can spark anticipation and is not presumptous.

18. What’s your opinion on sexting?

I think it’s great! It’s great foreplay and postplay

Post play?

Yeah, after sex, after the deed is done, send a text that says something like “Oh my god, it was so hot, I can’t wait to do it again” or take a picture of how you looked after and send it later. The key is to be creative.

19. How can you tell if you’re ready to start dating?

When you start paying attention to the opposite sex, or the sex you’re interested in, in a sexual way. When that interest comes back, thats when you start dating again

20. Are there any dating rules that you think are outdated?

The 3 day rule. If you didn’t call me the next day after a date we weren’t EVER speaking again.

When it comes to dating rules, nothing is written in stone since we live in such a fluid time.

Some rules stay, like not taking someone home to meet the family on the first date, and some rules are subject to discretion.

You need to figure out what works for you.

21. Best piece of dating advice for my readers?

Have fun and enjoy the dating process.

Any random thoughts?

You know what I don’t get? Double-dating if it isn’t two couples?

You mean like…4 singles go on a date together?

Yeah, I still don’t understand that.

You know, on Okcupid, there are occasionally people who have double-date profiles and I always thought it was weird.

Why bring other people out on a first date?

Thanks Mom!

and Good luck out there

3 thoughts on “Mother Knows Best: Dating Advice from Mom

  1. Aw, I like her advice. I stopped using OkCupid a few weeks ago. My coworker showed me and I’m a big fan of that over the others in terms of actually meeting people vs. just entertainment. It has a different approach that feels less sketchy cause you and your friends essentially act as “wingmen”. I like that it helps you find things to do too. Skout’s okay too, but still has it’s fair share of creepers


  2. Thanks Vicky! I’ve been a loyal user of Cupid since…I think 2008 though I’ve used it off and on since then. That said, it still has a ton of sketchy people on it though. A great website (or app) is Hinge because you can only be matched with friends of friends (as opposed to tinder which incorporates friends of friends and random people.

    I just signed up for, maybe I’ll write a review. Thanks for the recommendations and the support


Your Thoughts?

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s