DEAR JANE: My brother’s sexy new girlfriend looked oddly familiar, then I remembered how I knew her

Dear Jane,

I went home to my parents’ house for Thanksgiving and brought my new girlfriend with me. I was really excited for her to meet them and my younger brother.

As we got on the train to go, my brother texted our family group chat saying that he was on the way and bringing a girl that he had just started dating.

It was classic my brother to spring something like this on my parents at the last minute and he always seemed to be dating someone new.

He’s 23 and I’m 30, so there’s quite a big age gap between us, but we live near each other and have always been really close.

When we arrived, we jumped out of the taxi, hugged my parents and I introduced my girlfriend. While we were all saying hello, my brother arrived too.

After I hugged him, I turned to his girlfriend to introduce myself. But when I looked at her, I had this really weird feeling I had met her before. I clearly stared a bit too long because my brother pushed me jokingly, so I just said hi.

But I couldn’t shake the feeling I knew her. Even her name, Emma, was familiar.

It was only when we sat down to dinner that night, and I was across from her, that I realized where I recognized her from: we had matched on a dating app.

And it gets worse. Before I got together with my now-girlfriend six months ago, I was single and hitting the dating apps hard. I had probably lowered my age range slightly more than I should have done.

I matched with Emma (who is 20 years old) and we started talking, things got more and more flirty until Emma ended up sending me some slightly racy pictures. I never reciprocated and we never met in person because things got more serious with my girlfriend.

When I realized the connection, I went bright red at the table and everyone looked at me and I had to pretend to be coughing.

Emma seems to have no idea who I am, but I feel absolutely terrible nonetheless. I don’t want to tell my brother or my girlfriend, it would be way too awkward, but I feel so weird keeping it from them too. Not to mention she’s so much younger than me.

Should I keep this to myself and feel awkward around her forever, or say it now and try to laugh it off?

Best,

Tinder Trickster

Dear Tinder Trickster,

Dating apps may feel like a smorgasbord of fun when you first join. There are so many attractive people to meet and, perhaps, quite a few are interested in you. 

But very quickly the people in these digital dating pools start to feel like they are disposable. 

It’s no one’s fault.  Some singles are on  the apps looking for a relationship, others are searching for a distraction. 

In fact, unless you meet up in ‘real life’ with your cyber dates, its hard to remember who you have chatted with and harder still to remember what you have discussed.

I recently had a date with someone from a dating app. When we moved our conversation to WhatsApp, I realized his contact was already in my phone, even though I had no recollection of him. We had clearly chatted before but I have no idea what we talked about. 

I say this only to explain why Emma doesn’t remember you, although you have clear memories of her (doubtless helped by the racy pictures). But neither of you have anything to feel guilty about.

Though, if any young women are reading this, please, please, please do not send compromising pictures to strangers. You have no idea where those pictures will end up.

Now back to you. I don’t think there’s a need to remind Emma of your earlier connection. You have done absolutely nothing wrong. And, the whole exchange between the two of you seems pretty anodyne. 

Though, if you were to bring it up, I suspect it would be something to laugh over rather than anything to get upset about. (I might leave out the bit about the racy pictures, just for the sake of ease.)

As for your brother, he’s young and meeting people. Let him make his own judgement about Emma.

Dear Jane,

I’m 35 years old and my mother just passed away at 55 after a battle with cancer. I have no full siblings and have never met my father as I was a secret love child, so I’m all alone now.

My mother’s brief relationship with my father ended after he proposed to his girlfriend and decided that their affair must stop once and for all. My mother hadn’t yet discovered she was pregnant, and after she found out, she was too ashamed to tell him about me and didn’t want to disrupt his ‘perfect’ relationship.

Through some light Facebook stalking, I found out that my father had four children with his wife, so I have four half-siblings who I’ve never met. It’s painful to have a whole family who I don’t have a relationship with, and who don’t even know I exist.

Based on their social media accounts, it seems my siblings are all incredibly close and spend a lot of time together as a family. My dad and his wife also still seem to be very happily married.

Before my mother died, I would have never dreamed of imposing on their family. But now I’m feeling overwhelmingly lonely and I long for a family.

I’m scared to reach out to my siblings and father in case they respond with anger or flat-out reject me, but a small part of me is hopeful that they will welcome me into their perfect family with open arms.

Should I take a chance and contact them, or avoid the potential pain and try to move on with my life?

From,

Secret sister

Dear Secret sister,

I’m sorry that you have carried this secret with you for so long, and I’m even more sorry about the loss of your mother.

I fully understand why you want to get in touch with your father and half-siblings, particularly given that you are now alone. 

I honestly don’t think there is a ‘right’ answer to this. One school of thought would advise you against reaching out, given the potential of causing chaos for your father and his family with the news of his affair and secret child. 

The second approach would say you should reach out, because your father deserves to know that he has a daughter, and your half-siblings should be aware of your existence. 

I know someone who was in a similar position. This person had discovered through an ancestry DNA test that her beloved dad, who died some years earlier, was not her biological father. 

Through some genealogical sleuthing, she found her real father and ultimately decided to reach out to him. 

Initially he wanted nothing to do with her, but after a while he was willing to meet. 

Now, some years later, they have a friendly relationship, and she has gotten to know her half-siblings. 

One of the reasons she felt it important to contact him was to find out about any genetic health issues.

In the end, her choice to make contact worked out in her favor, but a positive result was not guaranteed.  

If you do indeed decide to reach out, I suggest you do it privately and just to him. And, as hard as this part may seem, I would advise you to detach your feelings from his reaction as much as possible. It would be lovely if he does choose to accept you, but if he does not, that is something you have to live with. 

At this fragile time of your life, please think very carefully about whether or not you could live with this kind of rejection. It’s rare for these meetings to result in happily ever afters. 

My best advice would be to stop thinking that happiness lies in having a large family. Instead, find other ways to curb your loneliness. Whether that involves focusing on building your friend groups, or joining a grief group to work though your feelings about losing your mother. 

Whatever you decide to do, remember that your happiness is in your hands.