A
male
age
26-29,
anonymous
writes:HELP. I've recently started dating this girl virtually. Obviously we can't see each other in person because of the COVID rules but we'd been chatting on Tinder for ages and never got the chance to properly meet up so decided to have virtual dates on Zoom. I do really like her and we seemed to connect straightaway. She is a really amazing person and I could easily talk to her for hours on end. Sounds promising right? Except the problem I need help with is very big; I've actually slept with her Mum.It sounds appalling, but let me explain. It happened in 2017. I admit I used to put it about a lot back then and sleep around. Me and my mates were constantly out on the prowl hooking up with girls for one night stands. One time I met this older woman in a pub and we hooked up. Even though I was 22 and she was in her early forties the age difference didn't bother her in the slightest. In fact we had a brief fling and slept together a few more times. I'd always had a thing for older women so it was a lot of fun, wild in fact. But it only lasted a few weeks. Sleeping with an older woman was actually on my bucket list at the time, but I’m sure you’ll be pleased to know I’ve grown up A LOT since then and I’ve started focusing on having proper loving relationships rather than casual one night stands.Even though we never saw each other again I wasn’t going to forget her in a hurry, especially as she had a very peculiar surname. Low and behold the girl I’m dating just so happens to have the same surname which I thought was a coincidence but upon looking on her Facebook page a few days ago, she has this woman listed as her mother. I nearly fell off my chair. I really wanted to believe it wasn’t true but we had another virtual date last night and got talking about our families, and when I asked her casually about her Mum she just rolled her eyes and put her head in her hands. She said her Mum seemed to be going through a full-on mid-life crisis for the best part of 5 years ever since she and her Dad divorced in late 2015. She revealed her Mum currently flitters from one man to the next and went through a phase of sleeping around a few years ago. She said it all stemmed from the fact that her Mum had her first child aged just 16 and was married at 18, so missed out on her youth. Now that she was single for the first time in her adult life she was basically making up for all those lost years. Any lingering doubts I had that she might not be the one who I hooked up with back in 2017 were well and truly gone, it all made perfect sense.But what do I do now? Should I just tell her about it? I really can’t see it going down too well even though it happened long before we met, because she revealed that she and her Mum haven’t been getting on very well lately. In fact they fell out on Christmas Day and have barely spoken since. Even if they did get on fine I don’t think it would go down well any way. She wants us to meet in person for the first time on Saturday for a socially distanced walk and even started talking about future plans for us when we finally come out of lockdown, which I’m all for as well. Like I said I really like this girl and want it to work with her. She clearly wants it to. But I feel like I’ve already tainted the relationship before it’s even started properly. I could just keep it to myself but if I don’t tell her then how could she ever trust me if she did found out? I can’t exactly play dumb can I? I just haven’t got a clue what to do for the best. I kind of feel like this is Karma biting for the way I used to be. I’ll admit I used women. I was a player and I was selfish. All I wanted was some fun. It’s only now that I’ve grown up somewhat that it looks like I’m starting to pay the price for my behaviour. Advice please.
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male
reader, anonymous, writes (6 February 2021): Don’t you tell her a damn thing. She doesn’t need to know her boyfriend hooked up with her mom.
You should, however, end the relationship and move on. If you stay, there is no way it doesn’t come to light. Worse yet. You may very well be tempted to sleep with her mom or she might be tempted to screw you. Proximity is a dangerous factor.
“I can’t be with you. You’re amazing and hot, but this is a very bad time in my life. Please take good care of yourself.”
A
female
reader, anonymous, writes (3 February 2021): Tell her.Do not be surprised when she breaks up with you.I would because of the ick factor.It is to gross.
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A
female
reader, anonymous, writes (3 February 2021): I do not see this ending well for any of you.It is too bad that you did not meet this girl before you decided to impulsively drop your pants for her mother and for her mother to recklessly lift her skirt for you. And sorry, I may be a bit old fashioned here but her mother's behavior was pretty trashy. Not a good example to set for her daughter or anyone for that matter.Her daughter will not get over that. Her mother might be able to since she appears to be the type who can f*** without any emotional involvement and move on to the next. But the daughter is going to think that is downright creepy and she is not going to like it one bit. She will feel competitive towards her mom and likely pretty jealous. She may feel like she may not be able to measure up or compare or she may always be trying too hard to keep you. In all of those scenarios, she will never feel safe with you, even if it is in her subconscious. It would be way too much pressure. The foundation won't be there for a solid, healthy relationship. So why bother? It is in my opinion just like an affair. You had an affair with her mother. Nothing good can come of that, except a lot of future insecurity, resentment, anger and tension. I see it as a drama filled relationship full of arguments. Not only will you have a bad relationship with her but she will have a bad relationship with her mother. Knowing your mom had sex with your boyfriend is not something that ever goes away.So, I strongly urge you to make the right decision. I would not open that can of worms.Want to act like the mature adult that you claim to have become since those days? Then walk away. Do not say a word. Remove yourself from the picture and don't ruin the relationship between a mother and daughter for your own selfishness.
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A
male
reader, anonymous, writes (2 February 2021): Blimey I would not want to be you right now!
You have to tell her mate, and sooner rather than later. You're right, she won't react well to it at all. But at the very least it would sound best coming from your mouth and not her Mums when she inevitably meets you.
Be prepared for this girl to call the whole thing off to give herself time to process this bombshell information. Tensions between her and her Mum will likely increase as well. But if you are really serious about this girl you'll wait for her in case she changes her mind.
But like I said, tell her as soon as you can. At the very least she'll appreciate your honesty over the whole thing.
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A
reader, anonymous, writes (1 February 2021): You have to tell her. Seeing this from her mother's perspective; who only remembers the old-you! Not to say you've changed all that drastically in the span of only three short years! We can only take your word for that. Convincing her would be the challenge, not us! You didn't describe the epitome or personification of the greatest boyfriend material, and the past isn't really that distant!
It really all depends on how her mother processes this. She will eventually be in the picture. Doesn't help they're on the outs, now you're plopped in the middle!
Going into protective-mother mode (or just plain jealousy), her mum might feel compelled to interfere; and do her best to be a wedge between you. Thwarting any attempt to slither back into her life. The thought of you eventually also sleeping with her daughter?!! It's unflattering! Making her feel old, used, a poor image for a mother; and put-aside for the younger-version.
Your tryst might be a reminder of a bad-time in her mother's life; and an example of one of her most unfavorable indiscretions. You and her mother didn't meet under the best circumstances. You may trigger some bad memories, and be an embarrassment to either of them. Certainly her mother would be an embarrassment to her daughter, causing an even wider divide in their estrangement.
Prepare for a probable negative or grossed-out reaction from her daughter upon the disclosure. This has the potential of some seriously explosive drama, my friend! It only happens in the movies, porn videos, or in soap operas on TV!
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A
female
reader, Honeypie  +, writes (1 February 2021):
 Yikes.
That is really all I have to say.
I DO think you have to spill the beans to her. If she is OK with it, then by all means try dating her. But I think this is something that will ALWAYS be a negative.
There is just no way MOST young women would want to date someone who had "ducked" their mother as some ONS. As much as I love my mom, and I love my daughters, all I think is eww, just eww. Not about my mom or my daughters but the dude. (in this case you)
Someone who is willing to stick his pecker in anything with a pulse is just not very appealing to me. You might have outgrown that - thank goodness. But have you had STD's tests done? Are you clear of STI/STD's? Are you vaccinated for HpV?
For me, if I was this girl - you would be a hard pass. And if you lied (by omission) and I found out? Even worse.
I mean, come on. If you met a girl and she told you by the by, I ducked you Dad... still wanna date me? Would you say AWESOME! Sure!?
I think you might have to rethink this. Hopefully you haven't been sleeping with so many women in your area that you can't find one who isn't related to one of your "conquests".
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A
female
reader, Dionee'  +, writes (1 February 2021):
 You definitely have to tell her because if she finds out later on, things will be much worse. If I were her, I would not react well to such news. I doubt that she will laugh it off and continue on but regardless, she has a right to know. It's a really unfortunate situation to be honest.
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A
female
reader, anonymous, writes (1 February 2021): What a pickle! Firstly, I don't think you need to apologise or feel bad for going through a phase of one night stands. You were young and enjoying your sexuality, nothing to be ashamed of. The mum of this girl had as much to play in the encounter as you did. Obviously, if you genuinely see a future with this girl then you are going to have to tell her. At the very least if you ended up meeting the mum then she may recognise you too and that would be even more awkward. If it were me, I'd go on the date first and see how it goes. Although you've connected amazingly over video call, it doesn't mean you will in person. No point dropping a bomb like that on someone who you don't even end up liking that much. I think if you make it past 3 or 4 dates and still want to see her you are going to have be honest. Explain to her that you didn't tell her immediately because you wanted to see whether the connection was real between the two of you and because you feel like it is you didn't want things to get any more serious without her knowing. Stress that you were young and a bit reckless and that it happened a long time ago. I can't see her taking this news well, especially if she's in a bad place with her mum. However if this is the case, then it's not meant to be. Give her time to process it and if she likes you enough then she'll get past it. Good luck!
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