Ask Wendy

Who Initiates Communication Between Dates?

September 2, 2016
Who initiates communication between dates? 

After a first date, I would initiate contact. I’d write a quick email thanking him for the time we had. I did this to send the unspoken message it was safe to ask me out again if he were so inclined. These emails were always short; here’s a sample: “Hi Sean! I had a lovely time with you today. Thank you so much for taking me to the Legion of Honor Museum. I love that place! But my favorite part was sitting on the lawn getting to know you. You’re interesting. I hope you have a fun week ahead. Wendy”

Ball tossed squarely over his fence to pick up or leave behind.


How Long is the Courting Phase Supposed to Last?

September 2, 2016
How long is the courting phase supposed to last? ~ A Girlfriend in the Making

Dear Girlfriend,

This is a trick question because there isn’t an end date. I do, however, want to speak to the courting phase, so thanks for bringing it up! There’s universal consensus about what the courting phase means:

  • Everyone’s on their best behavior.
  • It ends, you’re committed, and while you’re not going to fancy restaurants all the time anymore, it’s okay to wear sweatpants.


May I create a new framework for daters to think about when they think “courting phase?” Permission granted? Okay, thank you, I will. (more…)

What is the Perfect First Date Spot?

August 30, 2016
Where is the perfect first date spot?

Dear Perfect,

Paris! Did that help? 

Okay so the real answer is wherever the two of you are together that’s safe and comfortable. It’s fine to meet in a café, a city park, or somewhere easy-breezy. No need to make a big production out of your first meet-and-greet date.

A good friend of mine once said, “But I want our first date to be special. I don’t want to tell our grandchildren we met at a Starbucks!” then she went on to several dozen more first dates trying to make each and every one of them uniquely memorable so she could have that romantic story to whip out. Perfect, she was exhausted, and ended up quitting dating for a while. (more…)

How Much Should I Say About My Ex?

Friday, June 16, 2017
Hi Wendy,

I’m dating this guy and I like him a lot. He’s asked me what happened with my previous marriage. I started to tear up as I talked about it and he could see I was about to cry going back over the memories and events. I really think I made him feel bad.

The divorce was very hard for me, nine years and he drifted away because of how much we worked away from each other (military). I don’t think I'll ever be over him but each day gets more manageable. So, what do I tell this guy without giving off this vibe that he will be second place?

Hey dater,

I don’t usually dole out advice to wait to date, but in your case, you may want to step back and ask yourself if it’s time or if it’s too early for you to put your heart out there. Right now, it sounds like your heart’s kinda not in your possession—your ex is still holding onto it.


How Do I Date as a Single Mom?

Tuesday, June 13, 2017
Hey Wendy,

I’m a single mom with a fourteen-year-old daughter. I recently started dating an amazing guy. We see each other once or twice a week, and every other weekend when my daughter is with her dad.

I feel like my daughter’s radar goes off any time I plan something with him. I get texts requesting mother-daughter time; shopping and other things. I feel guilty, and I don’t know how to make everyone happy in this situation. Help!

Hey Single Mom!

I’m not a mom to anyone other than my dog, so while I haven’t experienced what you’re facing exactly, I do know what it’s like to be asked for things from people I care about when I’m not in a position to provide. While it’s uncomfortable and might make you feel guilty, it’s important for you—and, more importantly, for her—to hold your space and to keep your plans.

Like all of us, your daughter has a need for attention. You say you’re away from her to be with him one or two times a week—that doesn’t feel like too much to me. I bet she’s away from you at least that amount of time to be with her friends.


How Can I Accept My Polyamorous Girlfriend?

Friday, June 9, 2017
Hi Wendy,

The love of my life is a polyamorous woman. I reluctantly accept her lifestyle with the understanding that she will involve me in her encounters somehow (watching, videos, audio, etc.)

The first attempt at this was with a former FWB. She forgot to record anything because things happened too fast. It took everything I had to be ok with this situation. The one thing I asked for she ignored.

When I confront her she starts sobbing saying she's sorry. I don't know what to do.

Hi friend,

It doesn’t sound like you’re all that cool with her being poly. And you don’t have to be cool with it—just don’t say you are when you’re not. I have some questions for you:

Question 1: How do you think it feels for your partner to be “reluctantly accepted” as she is in your relationship? Probably not that amazing, I’m guessing.

Question 2: Do you know if her FWB and/or other lovers are okay with your agreement? It would freak me out if I were being filmed or photographed for someone else’s consumption if I hadn’t 100% agreed to it beforehand. Are you certain they’re okay with being recorded, watched, etc.?


How Can I Keep Political Fighting Out of My Relationships?

Tuesday, June 6, 2017
Hey Wendy

My girlfriend of two years and I are in our 30s and have very different political views. While we’ve disagreed in the past, we’ve always seemed to be able to work it out.

We were at a holiday dinner six months ago and we ended up speaking with a close friend of mine and his girlfriend. Unfortunately, during the dinner, the topic of politics came up with my girlfriend being on one side of the aisle and my friend’s girlfriend on the other. It turned unpleasant and we all left at the first chance.

Recently I had a bunch of people over, and I invited my friend and his girlfriend. My girlfriend is upset because she was uncomfortable with their presence and thinks I care more about my friends than I do her. In all honesty, I thought enough time had passed that my girlfriend would be more open to seeing them, especially since my friend’s girlfriend apologized, but it wasn’t the case.

Should I have run it by my girlfriend before inviting them? Does she have a right to exclude them from our future events? Help!


Do I Tell His Wife He’s Cheating?

Friday, June 2, 2017
Hey Wendy

I just found out I was the “other woman.” I thought my boyfriend was single but apparently, he’s been married for four years. Do I tell her?

Hey Lady!

I’m sure I’ll lose the popular vote on this answer, but girlfriend to girlfriend, my advice to you is nope, you don’t tell her.


What Does “Dating Casually” Mean?

Tuesday, May 30, 2017
Hey Wendy

I went out on a few dates with this guy and everything went really well, but now I have no idea how to do the casual thing.

Here are the details. Date 1 we both agreed to keep this casual, but Dates 2 and 3 were back-to-back and seemed to be more on the serious side. We dove into some heavier conversation, and ended up having sex a few times on Date 3. The sex was great!

Date 4 was planned for that next night, but I think both of us were feeling like it was too much and he beat me to the punch and bailed at the last minute, but rescheduled for next week.

I'm not used to casual dating, but I really don't want anything serious right now. So, what's the "norm" for dating casually? How often do casual daters see each other? How often should I expect communication with him? I'm in no hurry to be serious with anyone right now, but I don't know the difference between a blow-off and someone treating this casually. Help!

Hey Dater,

The difference between a blow-off and casual can be tricky to distinguish at the beginning. Without history together, you’ve never experienced his level of integrity and sense of follow through. When a date is planned and he cancels last-minute, that could mean one of many things, and you won’t learn the real ‘why’ until you know him. So, time will help you understand the difference.

Casual dating means you get to go have good times with your date, and you two have no obligations to each other in between those dates. There’s no rule of thumb or norm for frequency; that’s something you two can hash out together based on schedules and mutual interest.

Now, throw sex in the mix and sprinkle it with Oxytocin (the bonding hormone), and it can get a bit messier. (more…)

How Do I Stop Comparing Myself to His Ex?

Friday, May 26, 2017

knows too much about the ex

Hey Wendy

I am having trouble with comparing myself to my boyfriend’s ex. Before I ever met him, I knew his mother. She would show me pictures of him and his ex-fiancé, and she talked well of her.

They were together for six years. They come from a small town where they were treated like a celebrity couple. I see old photos online where it seems like hundreds of people were rooting for them.

When it comes to past relationships, the less I know the better, but I knew all about this other woman before I ever spoke one word to my boyfriend, so I’m having trouble feeling like I’m not as good and won’t measure up.

Hey Girlfriend,

You are not competing with her. He is your boyfriend. He is not holding her up in his mind while running an analysis against everything you do to see how you measure up. “Hmm…Margie kept a cleaner house than Carrie, so I still like Margie better.” This. Is. Not. Happening. He’s also not in bed with you comparing your body to hers—I can just about promise you that. Men tend to just focus on one thing, one person, one act at a time, and when he’s in the moment with you, he’s in the moment with you.

I hear you when you say it’s uncomfortable knowing all these details about your love’s past relationship, but here’s the thing: He had a whole life before you showed up (just like you did). There were people around—some of whom he loved, hung out with, drank beers with, flirted with, kissed, wished he could kiss—long before you. He is entitled to a history.


How Soon Is Too Soon for Sex Talk?

Tuesday, May 23, 2017

sex talk way too early

Hey Wendy

Sometimes when I chat with guys online, they are quick to talk about or reference sex in our first conversation. That creeps me out. Here’s my question: I’m wondering if I should try and get used to it, or do something differently because sexual banter is okay, or is this a major sign to leave that person alone?

Hey Dater,

When a guy talks about sex in the first few exchanges before ever meeting you, he’s letting you know what he wants—and what he wants is, well. sex. He’s also telling you he doesn’t have enough regard for you (or he doesn’t have enough brains in his head) to not risk blowing it with you by bringing up boning before you’ve even gotten to beers (more…)

What If I’m Not His Type?

Friday, May 19, 2017

not happy with body

Hey Wendy

I have been with my boyfriend for almost a year. He recently admitted to me that he was generally attracted to a different body type than mine and that he sometimes finds me physically unattractive.

He now feels awful for telling me, and he likes me in every other way. He says he and I just click, he’s happy, and he’s never been in a relationship so long.

He also emphasized that this was not how he always feels about me, but fuck, what do I do with this? I am not an unattractive lady. I love him and I don’t want to lose him, but ughhh…

Hey girlfriend,

Wow, I’m so sorry! That must have been incredibly painful to hear and a real hit to your ego. Ouch!

I have good news and bad news. The good news is that there are plenty of guys out there who will be attracted to you just as you are. The bad news is that this situation is not good news for your relationship.


How Can I Get Him to Remember My Birthday?

Tuesday, May 16, 2017

Hey Wendy

My significant other of four years has forgotten my birthday for two years in a row. Today is my birthday and I just don’t know how I feel about this.

I don’t care about presents at all—like AT ALL—and he knows that. All I wanted was a greeting or acknowledgement that it’s my birthday, and nothing. He knew my birthday was coming up but just completely forgot that today is THE day.

He tried to apologize but just didn’t sound sincere (or maybe I just didn’t want to listen to his reasoning, not sure). Do I have the right to feel shitty or am I overreacting?

Hey girlfriend,

Happy birthday! Sorry he forgot. To answer your questions: Do you have the right to feel shitty or are you overreacting…


How Can I Avoid Online Dating Burnout?

Friday, May 12, 2017

online dating headaches

Hey Wendy

Online dating can wipe me out. Especially when it comes to email. I get tons of messages from guys that I’m just not interested in. Any suggestions on how to not allow the online dating process to not feel like a draining sorting process?

Dear Dater,

Popularity does have its downsides.

Here’s what to do: Before you open your inbox, try editing your profile. Toward the end of your blurb, say something like, “I look forward to hearing from you! I respond to those who write more than six words and fit within the online pull-down specifications outlined in my profile.”


My Boyfriend Doesn’t Want To Get Married, Help!

Tuesday, May 9, 2017

the marriage question

Hi Wendy

My boyfriend doesn’t want to get married anymore. We’re 28 and have been together for 11 years now.

It was love at first sight, but we lived four hours apart and that distance took a toll on our relationship. A few years in, I left my small town and went to live with him in the big city, but within a few months of being together we were on again / off again for about a year. He proposed but took the ring back 11 days later.

We are together again, and we recently moved a thousand miles away from everyone/everything we know, so he could pursue his career. Now he tells me he never wants to get married or have kids. I am fine with it, I guess. Is it normal for a guy to change his mind like that? He says he wants to spend the rest of his life with me. I am confused.

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