Dear Wendy
Dear Wendy

Five Questions about Dating with Two Professional Matchmakers


Linda Kassimir Murad and Liz Murad Waters, owners of the matchmaking service, The 2nd Date, in Los Angeles have successfully set up lots of couples over the years. I asked the two (who happen to be cousins by marriage) their thoughts on the best way to find a match, what people should look for on a first date, the biggest mistakes people make on their journey to finding a match, and when you should express that you’ve fallen in love. Here are their insightful answers:

DW: What do you think are the biggest mistakes people make on the road to finding a match?

Linda and Liz: Some of the biggest mistakes are being too picky and looking for the perfect fairytale romance. In real life, the most important things in a partner are whether they have your back, will they stick up for you, will they nurture you and the relationship, will they put in the work necessary to make a lasting relationship, and, probably most important, will they put you first? People who are too caught up in someone’s appearance may be missing out on some amazing people that they could ultimately become attracted to because of who they are inside. We often interview potential clients who say they refuse to date someone with 5 extra pounds or someone under 5’10”, but people should really focus on the qualities that are going to hold you together through potentially tough times, like illnesses and job loss.

DW: Where is the best place or the best way to look for a match?

Linda and Liz: The best place to look for a match is through a friend. This way the person has hopefully been vetted and doesn’t have any major skeletons in the closet! We also think meeting someone while doing an activity you love is a great way to meet someone. So if you love art or photography, take a class; if you love to hike or run, join a group! We also tell people if you are meeting friends for dinner, maybe plan to arrive 20-30 minutes early and order a drink at the bar. That way you aren’t really going out alone, but you are more approachable than if you are sitting at a table with a group of friends.

DW: What questions should you ask on a first date?

Linda and Liz: You should keep things light and fun on a first date, while also subtly investigating whether you have shared interests and life goals. For example, if you love to be on the go, you want to find out if your date is a couch potato, or if you are a foodie and love red meat, maybe a vegan is not ideal. You can often find out a lot about someone by asking different questions, like What do you like to do on Halloween?. As we said before, another telling question is as simple as What did you do last weekend?. We definitely wouldn’t recommend asking questions about exes, politics, or other controversial subjects on a first date.

DW: How does age play a role in dating? Is there a certain age or “age difference” to aim for?

Linda and Liz: Age is less important than whether you are in the same place in terms of life goals. We would typically encourage women to look for men up to twelve years older although, again, we don’t feel age should be a deciding factor. We just want people to be open-minded and open to getting to know the other person. Often men get stuck on age because they want children, but many women are now freezing their eggs and technology is rapidly changing, so that should be less of an issue.

DW: When should you express that you’ve fallen in love? When is the right time to “define the relationship”?

Linda and Liz: We wouldn’t suggest telling someone you’ve fallen in love too early as that could potentially scare someone off and can also change the dynamics of the relationship, and we advise waiting at least until you have been in an exclusive relationship for three months. As for defining the relationship, we would recommend doing that before you decide to get intimate with someone. You should at least establish that you like each other, intend to keep dating, and are not actively seeking other relationships.

You Might Also Like:

20 First Date Mistakes to Avoid
Dating Tip: Try Going Against Type,
A Timetable for Relationship Milestones,
“Was it a Mistake to Sleep with Him on our First Date?”.

48 comments… add one
  • kmtthat

    kmtthat May 1, 2018, 10:38 am

    This is interesting. I do think that the comment on doing activities you like to meet people to date is a little unfair (or over simplified). As a woman who likes to do things just to do them, there was always guys who were clearly on the hunt at salsa class/improv class/softball. And inevitably, you’d still have to see them at class next week after they’d asked you out, and it was always awkward. I just want to draw/blow glass/make robots without it feeling like a bar? I think it makes more sense to tell people to be the kind of person you want to be with – don’t wait for a partner to do all those things you always say you want to do. In the process of growing yourself, you often grow your social circle. You may meet someone at a new friend’s housewarming, or going to a new art gallery that someone from your sculpting class recommended. That doesn’t mean “take salsa class to meet women.” Too many people say they want somebody with qualities they actually wish they had themselves (“they need to be successful and make $X” when they are not ambitious, or “they need to be no more than a size X” when they are out of shape). Like attracts like, so be the kind of person you want to be with.

    But meeting through friends can be tricky too, as they can get over involved in your budding relationship (telling you about their exes, or if it’s a couple pushing you to be bf/gf so they have a new couple to hang out with). And the inevitable awkward of seeing them post “so sorry, not interested” or breakup since they are part of your friend’s social circle. Cue to me in as a bridesmaid and my ex as a groomsman in mutual friends who hooked us up’s wedding. Which, if everyone is mature adults, not a big deal…but still a thing to think about if it’s a close friend of a close friend.

    For these reasons, I met my bf on Tinder, and it was great. We were able to introduce each other to new hobbies (hockey is actually fun to watch!) and new social circles. And there was less awkward likelihood of having to continue to see him if it didn’t work out. I guess matchmakers wouldn’t recommend dating apps since it’s literally their competition, but I do think they are improving by and large and the majority of my friends entering new relationships are doing so through people met originally on apps. And that’s ok!

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  • avatar

    JD May 1, 2018, 11:43 am

    I agree that being set up through friends is just a recipe for disaster. It doesn’t work out, the other person is at events, friends are overly involved in your relationship. It has completely sucked in my experience and caused lost friendships.

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    • Dear Wendy

      Dear Wendy May 1, 2018, 1:40 pm

      I married the one and only guy a friend set me up with, so success story here.

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        JD May 2, 2018, 9:52 am

        NICE! I offered my new neighbor/now husband a ride to swap his Uhaul for his car when he first moved in. You know since you can’t drive both at the same time. Halfway through the drive I thought “why did I just offer a strange man a ride alone in my car”….glad I did though.

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  • Portia

    Portia May 1, 2018, 11:56 am

    I think “meeting through friends” can be very tricky. My husband is no longer allowed to play matchmaker because he has a record for setting up some spectacularly bad matches. I try not to as well, though my friend groups don’t all know each other and a few hook-ups have happened as a result of a party or something where we invite people from different friendship groups (nothing lasting more than a hook-up really). I haven’t lost friendships over it, but there’s been some awkwardness.

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    • Portia

      Portia May 1, 2018, 11:58 am

      Oh, but I highly endorse looking for love at a class or other activity group. I know a bunch of successful couples that met through meet-up or a sports league.

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      Fyodor May 1, 2018, 12:04 pm

      I think that being “set up” through friends where they schedule a date is not a great idea. I think that *meeting* people through friends, where the common friendship gives you a chance to socialize in a lower-pressure, more organic way, can be a good way to meet people.

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        ktfran May 1, 2018, 1:14 pm

        I’m with Fyodor. It’s a great way to meet people! I’m not great at first impressions. I’m shy and I often had a hard time asking questions, etc. Dating sites were not my jam.

        Nearly every successful dating relationship I had was from either meeting a friend of a friend/cousin, or through work. When I’m hanging out with people in a chill setting, I shine. There were never hard feelings when things didn’t work out.

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        csp May 1, 2018, 1:54 pm

        I totally agree with this. I met my husband by being out with a friend. This friend and my husband went to high school together. They bumped into each other, started chatting, and we met. It wasn’t planned but it was an easy introduction.

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      • Portia

        Portia May 1, 2018, 2:40 pm

        I’ve only had luck with being the conduit to a friendship that way, not a romantic relationship. The romantic encounters where me and my husband are like, let’s invite these two because I think they might be a good match, either don’t work out or occasionally end very badly. I think only once has it been an actual set up (also ended badly). I don’t even try anymore and I decline to set people up when asked…

        I think something similar to the way I met my husband is how I’ve seen it work well. You have a house party or other semi-organized gathering with some loose connections, so you have a little to talk about, but you don’t have a matchmaker or even necessarily someone else knows both people well. For us it was the first week of college so no one really knew each other yet and we had a handful of loose connections which is why we ended up in the same location, but no one was vouching for anyone else really.

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        SpaceySteph May 1, 2018, 2:51 pm

        I went on one actual set-up and it was terrible. Complete personality mismatch, he didn’t find me funny, I found him smarmy. Just no.
        My husband I met through friends but not as a set-up, just a friend of a friend who happened to be at the same party.

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      • Copa

        Copa May 1, 2018, 4:47 pm

        Agreed. One of my worst dates (not terrible, just super boring and awkward) was with a friend of a friend. We were set up on a blind date. But at a BBQ a couple years ago, I hit it off with my friend’s brother’s college friend. We went out a couple times. It was pretty clear our overall values/goals were mis-matched, but it was nice that we were able to meet in a low-pressure situation and things progressed very organically. It wasn’t/isn’t awkward with mutual friends.

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    • Copa

      Copa May 1, 2018, 4:50 pm

      Whenever I ask friends to set me up, I get the same response: “I only know single women, not men.”

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        Fyodor May 1, 2018, 5:01 pm

        I think that unless, you’re like an Orthodox Jew, the men aren’t really looking to fix their male friends up, so assuming that each half of the couple has mostly same-gender friends there tends to be an imbalance.

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      bondgirl May 2, 2018, 10:44 am

      I actually met my husband-to-be through mutual friends. They even crashed our first date! Though if it didn’t work out I think we would’ve been able to still hang out with said mutual friends without it getting awkward since there’s only a few of them whom we don’t see too frequently. So I do agree with Portia, that meeting through friends can get tricky…but I think it’s very circumstantial. Depends on the group of friends, depends on the individual personalities, etc.

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  • Moneypenny

    Moneypenny May 1, 2018, 11:56 am

    It’s funny, in my experience, whenever I’ve participated in activities to be more social (like on meetup, pick-up sports, classes, professional events/public affairs events), I have seldom met men who were on the hunt, like kmen says. I always left feeling glad I did whatever it was since it was fun and I usually met really nice people, but never did it ever lead to any dates let alone any flirting or anything like that.

    The area I live in is already supposedly one of the toughest dating markets (so I’ve heard, and certainly experienced for myself), so maybe that has something to do with it. (Or maybe it’s just me? heh…)

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    • Moneypenny

      Moneypenny May 1, 2018, 12:01 pm

      I also agree on the trickiness of dating through friends. I am always up to meet the friends of my friends, generally speaking, because that’s how you make new friends! But dating is tricky. I once dated the brother of a friend of mine, and it ended up being a total disaster. I also wished my friend had warned me about certain things (like how recently he had just broken up with his very serious gf) because in the end, I didn’t realize I was the rebound and it was really painful. And it made things awkward between my friend and I for awhile.

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    • avatar

      Fyodor May 1, 2018, 12:06 pm

      Probably depends on the ages too. I don’t know of anyone who did like a mid-20s kickball league that wasn’t a big hookup-fest. For stuff in your 30s, you probably get a better mix of people who are already coupled off that are there out of genuine interest.

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      • Moneypenny

        Moneypenny May 1, 2018, 1:31 pm

        Yeah, I totally can see that being the case. Just speaking from my own experience, when I was 25 I think, I played softball and people just didn’t mix outside of their own friend groups. I have seen it too with other mixer type things – it’s almost like being back in high school!

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    • kmtthat

      kmtthat May 1, 2018, 1:31 pm

      Eh, I think it’s also me a bit. I tend to be very friendly, ask people questions about themselves, remember details they’ve mentioned, crack jokes, try to get everyone to go to a bar after, etc.. All of which can seem flirty even when I am totally not intending to be. I’m also relatively conventionally attractive and like to dress up, so maybe I looked like I was trying to get attention. I do have some great guy friends that I met through an activities and have never hit on me (but definitely check out my friends, who I’m like he’s such a solid dude!)

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      Fyodor May 1, 2018, 4:18 pm

      I’m curious what you mean by “toughest” dating market-not challening, just genuinely curious. I’ve been in places that seemed easier or harder for men or women but I was never sure how much of what I saw/experienced was representative.

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      • Copa

        Copa May 1, 2018, 4:37 pm

        I think generally speaking, major cities are thought of as being tougher dating markets because there are seemingly endless options. I’m in a major city, and I think it’s a hard. That said, I have friends in smaller cities or more rural areas, and they have to widen their search to a fairly large geographically area. It certainly doesn’t seem ideal. I think it’s hard to quantify and compare dating markets. Dating is hard all around!

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        Fyodor May 1, 2018, 4:53 pm

        Yeah, I wonder if there just isn’t a lot more publicity/attention about the woes of dating in the big city. That’s where the publications are.

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      • Skyblossom

        Skyblossom May 1, 2018, 5:32 pm

        I grew up in a very rural area. The closest town had a population of just over 400 people. Four towns combined managed to have a high school of just over 100 students and by the time I graduated from high school there weren’t even that many.

        Whenever a new female teacher arrived in town all of the unmarried farmers would try to date her because there were so few women to marry. Most of the young women would either marry straight out of high school or go away for college or jobs. The young men who stayed to farm ended up with almost no one to date if they didn’t get married within a year or two of graduating from high school.

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        JD May 1, 2018, 7:39 pm

        I lived in a major city and yes the endless options seemed to make it worse. Why commit to anything when there are 1000 others waiting in line. I am quite sure that if I lived somewhere different I would have been married long before. That being said living there brought me to my husband so well worth it.

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      • Moneypenny

        Moneypenny May 1, 2018, 8:44 pm

        Yes to what everyone else said above!
        I will also add, I live in a city/metro area where a lot of people move for a particular job market but don’t intend on staying and settling. A lot (not all!) are not looking for anything serious because of that. Peter Pan Syndrome. Or, they’re really focused on making it big in their career. Again, not everyone is like this (I did meet my boyfriend on Tinder of all places!), but there are SO MANY men like this out there in my area.
        I don’t mean to imply that, say, smaller cities or more rural areas don’t have their own dating woes as well- they probably do, but just for different reasons!

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        Fyodor May 2, 2018, 8:02 am

        I am about 80 percent sure I know what city you are referring to, having previously lived in a city described repeatedly in very similar terms (I assume that naming the job market would give away the city). It is from a lot of accounts an unusually difficult place for women to date.

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      • Moneypenny

        Moneypenny May 2, 2018, 11:47 am

        Fyodor, now I’m curious what city you’re thinking of.
        It’s a particularly hilly (and expensive) west coast city. 😛

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      Fyodor May 2, 2018, 11:54 am

      I was wrong- was thinking of Washington DC , where I once lived, which famously has a lot of people come for government/nonprofit work and was somewhat less famously is a difficult place for women to date because of the male/female ratios.

      I ALSO lived in the place you are referring to, which at least when I lived there (fifteen years ago), was kind of the opposite, because of the oversupply of male engineers in the technology industry.

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      • Copa

        Copa May 2, 2018, 11:58 am

        The phrase “the odds are good but the goods are odd” comes to mine when I think of an oversupply of male engineers. 😉

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      • Moneypenny

        Moneypenny May 2, 2018, 12:00 pm

        Ahhh, gotcha! Nope, there are a lot of men out here, but weirdly, it’s not as easy as you might think- as Copa says, the odds are good, but the goods are pretty odd. (Or at least, socially awkward. Or totally full of themselves. My friends and I could tell you some stories! 😛

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        ktfran May 2, 2018, 12:05 pm

        I honestly don’t know why engineers get such a bad rap. I’ve worked for an engineering firm for 15 years, and sure, there’s a few oddballs here and there, but most of them aren’t. There are so many cool engineers, both when I worked in FL and now… so completely different areas. And those that are coupled up have super cool wives and husbands and friends. I’d say the ratio of odd to normal is 1:3. One being odd/stereotypical. 3 being relatively cool. We have some super brilliant people too, that aren’t oddballs at all.

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        ktfran May 2, 2018, 12:08 pm

        I also work for the largest A/E firm in the U.S. 85k people. So it isn’t a fluke/one kind of engineer.

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      • Moneypenny

        Moneypenny May 2, 2018, 12:17 pm

        Well, to be fair, I should have said some, not all. And I get it, I work with engineers a lot as well (structural, MEP) in my job. Like I said in my post above, it’s some, not all. There just happens to be an abundance of technology workers here, which tends to skew things quite a bit. It’s not unusual anymore to walk into a bar and 80% of the bar is male and wearing hoodies, whereas 10+ years ago (when I started going to bars, ha) the demographics were quite different.

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      • Copa

        Copa May 2, 2018, 12:41 pm

        It’s a sweeping generalization and I’m kinda kidding. I’ve met plenty of great engineers, but the oddball engineers I’ve met have been memorable. I think it’s one of those professions that attracts people with similar qualities, and yeah, I do find a lot of engineers on the socially awkward side. (I don’t think this is automatically a bad thing unless someone really doesn’t mix well socially.) It’s kinda like how I’m a lawyer but openly say most lawyers are jerks. There are actually plenty of great ones out there; I think I’m a nice one, and I know and interact with plenty of funny, kind ones on a daily basis who outnumber the ones with the larger-than-life egos. Even though I know this, when I see them on dating apps, it’s almost always an automatic NOPE! Swipe left!

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        ktfran May 2, 2018, 12:46 pm

        Fair enough!

        I’ll admit, I used to think people who worked in finance were total d-bags/bros. Only because a lot of them I met at bars were. I’ve since amended my thinking.

        I would just hate for someone to see occupation: engineer (or for me, finance) on a dating site or wherever and not give the person a chance because of preconceived notions.

        I’ll also admit that I’d LOVE to see how a few of the people I work with interact socially. Because yes, there are some oddballs.

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      • Copa

        Copa May 2, 2018, 12:58 pm

        I’ve dated a bunch of finance guys and consultants, and I think you have to have a more sociable/charming personality in those types of jobs. The same qualities outside of work can come off as douche-y and insincere.

        I work with/around attorneys and law, but don’t practice. I’ll tell people what I do and I omit the lawyer details as long as I can because I don’t want to be lumped in with the personalities I dislike.

        I figure people might swipe left on me for a lot of reasons that are fairly stupid at the end of the day, but that is what it is.

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        Fyodor May 2, 2018, 1:29 pm

        Even given all that, I’d say that it was pretty unusual to meet a reasonably attractive woman in the bay area who wanted to be married who wasn’t. Whereas it was very common in DC. I had plenty of female friends who seemed to be good catches who were struggling to find someone.

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        Fyodor May 2, 2018, 2:25 pm

        I’d say that in the bay area it was a lot rarer to meet a woman reasonably together/attractive who wanted to be in a relationship/married and wasn’t. Whereas in DC and other east coast cities I knew a lot of women who seemed to be good catches who were struggling to meet someone. There are even matchmaking services that try to connect women in manhattan with men on the west coast.

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        Fyodor May 2, 2018, 2:25 pm

        sorry for the double post.

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        Fyodor May 2, 2018, 2:26 pm

        There are lots of different kinds of lawyers, but I’d say that of the lawyers in private practice in law firms that I have worked with, something like 1/3 are divorced or have seriously messed up marriages.

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    csp May 1, 2018, 1:59 pm

    Overall, I think the take away with “activities” in general is to go somewhere new. If you go to the same bar on the same nights you see the same people. If you hang out with the same friends doing the same things, you aren’t meeting new people.

    I also think that people tend to stay in their gender corners too much. What I mean is that if women go to wine tastings and painting with a twist, you are going to see more females or couples. If men stay at sports bars or hooters, you are going to see more men. My one girlfriend decided to only go new places for a few weeks, take out, bars, clubs, events, to shake things up and she found things much better when she got out of her normal routine.

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    • avatar

      Alex May 3, 2018, 7:01 am

      Start from this to get him hours and after use him as you wish!

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  • Cleopatra_30

    Cleopatra_30 May 1, 2018, 2:43 pm

    I was set up by a friend with her then BF’s friend many years ago. It did not work out, he was not my type physically or personality wise. He then blew up on me after I ended things after 3 or 4 dates (He had recently left the army and had some unresolved issues).

    I think it didn’t work out cause my friend didn’t share the same interests as me, and therefore wasn’t looking at this person through a similar lens. I think that is something to consider as well when your friends try to set you up, if you are confident your friend knows you well enough, then they would be good for keeping an eye out for men they know. Otherwise it will probably be a crap shot.

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      Fyodor May 1, 2018, 4:15 pm

      I’ve certainly known a lot of people who think that if they have two single friends that those friends should be coupled off, independent of whether they are compatible. The people to be suspicious of are ones who have been coupled off for a few years and miss the novelty of dating. After you’re coupled off long enough you stop doing this and become like some ancient monster that doesn’t know how to relate to the modern world and stop.

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    SpaceySteph May 1, 2018, 2:56 pm

    I think its not just about having similar interests as you but also look for similar things in a SO. Not everyone values the same thing in someone they’re dating, and one girl’s “slightly annoying thing but I could live with it” is another girl’s “I will kill you if you do that one more time.”

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  • avatar

    000 May 2, 2018, 6:19 pm

    I’m curious about the age-related advice. All we heard was how much older men women should date. What about how much younger men? What about how much younger/older women men should date?

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