When he agreed to my bold request after our first date, I got the instant ick. He’s the first man to fall for my trick… even though every woman does it: JANE GREEN

Dear Jane,

I matched with a guy on a dating app a few weeks ago and, after hitting it off over text, we decided to meet.

He planned the entire evening. We went to a fancy restaurant and spent three hours chatting.

We have so much in common, and he seems like the perfect guy. He has a great job, owns his apartment and enjoys all the same activities that I do.

Basically, everything was perfect… and then the check came.

Like the lady I am, I offered to split. I always do, but no man has ever actually taken me up on it. But he did!

We both had four drinks and a three-course meal, so it was a hefty bill: almost $200 each.

I would never have chosen such a fancy restaurant if I knew I’d be paying, and he was the one encouraging me to order more drinks and get dessert. He also has a way better job than I do, which he knows.

I think this is a massive red flag. Men should always pay on the first date, especially if they make more money and picked the restaurant.

If I’m honest, I want to ghost him… but I genuinely really liked him and enjoyed spending time with him. It makes me sad to think I might never see him again.

Should I give him another chance?

From,

Checked Out

Dear Checked Out,

The rules of modern dating have indeed changed, and while it’s not unreasonable to accept an offer of splitting the bill, given the inequality of the choices he made, I completely understand why you feel taken advantage of.

Rather than a red flag, I see this as more of a problem with communication. 

Given that he set the tone of the evening, took you to an expensive restaurant rather than a more affordable date of getting a drink or grabbing coffee, I, too, would have expected him to pick up the bill – as old-fashioned as that might seem.

While he is great in every other way, and sounds like someone you want to see again, it may be that he doesn’t share the same values as you.

But this isn’t something you will know for sure until you get to know him better.

Modern dating can often feel speedy, particularly when you meet on a dating app. There is an enormous amount of ‘love bombing,’ in which men are more in love with the idea of love than in taking time to get to know someone, and overwhelm women with a romantic fantasy before suddenly shutting down and disappearing.

And when we meet someone who appears to be everything we’re looking for, even the most hardened among us can find it hard to resist.

But the only way to find out who people really are is to take our time and get to know someone slowly, and, in your case, communicate how you feel after what was otherwise a perfect first date. 

Should he call again and ask you out, that’s an opportunity for you to tell him that, sadly, you can’t afford the kind of dinner that you had the last time, but would happily meet him for a drink.

Then, you can figure out how intentional he is about finding someone. And, rather than telling him about you, show him how wonderful you are. Ask the important questions. Listen carefully to his answers. 

That will tell you whether or not he’s the sort of man you actually want to spend time with.

Dear Jane,

I recently got engaged to my boyfriend of three years.

My fiancé has a sister who is two years older, and we’re not particularly close. However, he told me it would mean a lot to him if I asked her to be my bridesmaid, and I agreed.

I also have a sister who is two years older – we are very close, and I have asked her to be my maid of honor.

The issue is, both of the women have very strong personalities and are butting heads while wedding planning.

My sister is constantly complaining to me that my in-law is trying to take control of planning the bridal shower and the bachelorette party, even though those are supposed to be maid of honor duties.

My sister-in-law also invites herself to every single wedding planning event – she came to all my dress fittings and even showed up at the cake tasting.

I see why my own sister is frustrated, and honestly, I’m getting a bit frustrated too. This is ruining my wedding planning experience.

Would it be awful to tell my sister-in-law she can’t be a bridesmaid anymore? We’re not good friends, and I don’t really care if I burn the bridge between us.

But I obviously don’t want to upset my fiancé, and I think this decision would hurt him.

Should I prioritize my bridal experience and my happiness, or bury my feelings for the sake of peace?

From,

Bridesmaid Wars

Dear Bridesmaid Wars,

What a difficult situation you are in. It is painful when someone oversteps boundaries without realizing the havoc they are creating, but what’s harder is the lengths we will go to avoid having a difficult conversation.

Rather than telling your fiancé’s sister she has overstepped, you are thinking of cutting her out altogether.

I see this issue as more nuanced.

Removing her as a bridesmaid will damage your relationship with your future husband’s family irrevocably. There is an old saying, beware of unintended consequences, and I can’t think of any good that will come from telling her that she can no longer be a bridesmaid. 

You may not care about burning a bridge with her, but I suspect it will cause damage to the relationship you have with your fiancé’s entire family, not to mention create friction between the two of you.

As hard as it may be, the best way forward is to take your future sister-in-law out, perhaps for lunch, and tell her that you are trying to keep everyone happy, which is proving to be an impossible task. 

Tell her that the maid of honor’s duties include organizing the bridal shower and the bachelorette, and, as such, you are trusting your sister to organize that on her own. You can always add that if your sister needs help, she will let your sister-in-law know.

As for her showing up to the cake tasting and dress fitting, I have to imagine that your future mother-in-law was there as well, and perhaps others. I’m wondering if you can think of this differently and find compassion for a woman who wants to be involved in a family event that she is clearly excited about.

Ultimately, I think you have to pick your battles, the big one being her interference with your sister’s roles and making your sister feel marginalized. Rather than cutting your sister-in-law out, be clear with her – in a friendly way – that this is your sister’s role. Thank her for the offer, but tell her that your sister is fine doing this alone, and will make it known if she requires assistance.