Wendy Williams knows dating can be tough. Even though she’s been (happily) married for 18 years now, the host of the Wendy Williams Show is constantly hearing about the trials and tribulations of trying to find love from viewers and friends. From too much texting, to women jumping into bad relationships too quickly, Wendy has seen it all — and luckily, she’s partnered with the Cut to give our readers some much needed love advice, just in time for Valentine’s Day. We opened our Instagram DMs for dating questions from our readers, and they came back with some universal problems many of us can relate to.
Here’s what Wendy has to say about long-distance relationships, getting back into the dating game, and whether you should tell your flirty friend you have a crush on him or her.
Hey there — I have a question for Wendy. So I met this guy on OKCupid and we hit it off, went on a date, had an amazing night the next day (sex), but he had to go back to work to another country. He still texts me, we flirt, etc. I know he’s into me, but am I stupid for thinking this might work? How do I even ask — should I even ask him if there’s something here and if he wants to take this long distance? Thank you!
Long-distance relationships are such a dicey thing. And when I say long distance, I’m talking if you live in Elizabeth, New Jersey, and he lives in Great Neck, Long Island. People can barely manage that distance. A whole other country for me is a big no-no. For what? You don’t even have a reason to put effort into the relationship because you’re young (I’m assuming), you don’t have children with him, and it would just drive you crazy. It’s very expensive, and once you leave to visit him, you might never be able to come back, if you know what I’m saying (and I think you do).
Hi, Wendy! How would you handle a man who stonewalls you and gives you the silent treatment? I’m becoming extremely frustrated and sad about this, and we have only been dating two months. Thanks! Xoxo
If you don’t like it, now’s the time to bail. I always say to single people: Date a lot, date often, date outside of your type, date outside of your race. Just date, date, date, because you have to kiss a lot of frogs before you find your prince. But, with that said, three is the magic number. By the third date, you know if you want to go on a fourth date or not. By the third month, if you’re not feeling butterflies yet, then you never will. There are some people who are in love by the third month, or can say “I love you” by the third month — I’m not necessarily pushing that, but what I’m saying is, you’ve only been together two months and he’s stonewalling you? And you’re complaining? Move on to the next guy!
I have a crush on one of my friends, but I am afraid of letting them know in fear of ruining our friendship. He flirts — he’s a natural flirt though. What can I do to see if he’s on the same boat as me without telling him? Or should I tell him?
You left out a lot of really pertinent information. How long have you been friends with him? Because if you’ve been good friends with somebody for three years and they flirt with you, but they flirt with everyone else, but he hasn’t singled you out, then he’s not into you like that. Don’t be offended, it’s just what it is. You’ve got to know how to read the signals of people around you. A key piece of information is that you said he flirts with everybody, so you’re just another girl.
I need to know how long you’ve been friends with him. I’ll tell you this right now — chances are, he’s not into you, even if you’ve been friends with him for a month. People who like other people in an attractive way, you can’t hold that in. You know the signals. I wouldn’t tell him. It’s going to make things weird. He’s not into you.
Hello, Wendy. How you doing? Okay, I’ve been married to my hubby for 37 years and I’ve run out of things to do as far as gifts, dinner. As for time alone, we get lots of playtime — both adult children are grown and live on their own — so time alone isn’t a problem. I just have no clue what will be good to surprise him with at this point. Oh yes, I’ve done the romantic trips with the hotel-room-décor sexiness. He’s so into sports after work … I have no clue, please help me. P.S. The sex is still the bomb. I’m 56; he’s 60 and sexy with no blue pills. Hell naw.
I love that. Your life sounds like the kind of life that everybody wants to be living once they become empty nesters. They’re perfectly happy, they spend a lot of time together, the sex is still good. But you’re looking for something to do for Valentine’s Day? You’re asking the wrong person! We don’t celebrate Valentine’s Day — okay, okay, I’m out of the closet with it. I feel like every day is supposed to be Valentine’s Day, in its own weird way. You need to be kind to one another. When he sneezes, you say, God bless you. When you use the last piece of toilet paper on the roll, put the other one on the spring — don’t sit it on the table. Putting it on the spring means, I love you. To me, little things mean I love you, and after being married for a long period of time, it is hard to come up with those things.
Why don’t you watch sports with him on Valentine’s Day? And put out a couple of snack trays. Just keep it real simple. People put a lot of pressure on themselves for Valentine’s Day. It’s too much. I don’t care about a card. You know the only person who sends me a Valentine’s Day card? My mom, ever since I was a little girl. I’ve always said the same thing, even when I was a little big-mouth girl, and I say it to my father, I ask him, Why is your old lady buying me a card? I’m not her problem, you’re her problem on this day. Get out of here with that! Stop sending me mixed messages. Valentine’s Day is not about mother-and-children relationships. It’s about the romance. I don’t give my kid a Valentine’s Day card, and I don’t want him to give me one.
Dating over 50. Men just act like teenagers. Booty calls? Hell, if any of us wanted that, we can. If we choose to do that. It’s not easy getting back into the dating scene. How do I go about it? Help.
You go about it with both eyes wide open. You’ve got to watch social media, because social media is the breeding ground for liars. People who say that they’re taller than they are, guys who act like they have a big-shot job when really they’re working at the bodega instead of owning the bodega, and women lie, too. How do you get back in? Just jump. Don’t date too young, because they might expect some things from you. If you’re dating a 35-year-old man and he has no children, what if you fall in love and he wants children? You know our eggs are fried and scrambled at 50, so we can’t give that. Just be careful.
If I were a single woman right now, I’ve got to tell you something, I’d be prepared with lip gloss every time I leave the house, not because I have a full face of makeup on but because you want to give a reasonable presentation to let the world know you care about yourself and you are available. Eye contact is very important; bat your eyes. Don’t wear wedding rings on your fingers unless you’re actually married — a lot of people do that, girls specifically. I don’t know why. It’s stupid. I always call it soiling, like why are you soiling the finger? You’re sending mixed signals.
I don’t know whether you’re into dating outside your race or not, and I don’t know whether you’re into dating short guys if you’re really tall, but I would at 50 something. It’s not because I’m desperate. It’s because you’re looking for a good time at 50, you’re looking for great conversation at 50, you’re looking for somebody who can take you for a decent meal at 50 years old — somebody who can at least split the tab for a vacation to Hawaii or something. And first dates should never be where he’s picking you up at your house. Don’t let him know exactly where you live. That is a big deal, there are a lot of crazy people out there.
And watch for married people with full families lying about being single. Don’t mean to scare you, girl. Welcome to the jungle.
I want my ex back even though I know we have different long-term goals, which is why we amicably broke up. Until recently, he had tried to get back together with me but now he seems to have moved on — but I’ve had a change of heart and want to try again. He said he’s confused and wants to think things over, but is now acting distant and I know he’s going on dates. Should I take this as a sign or should I keep fighting to get him back?
I’d call him up and get together with him. Since you know him, this can be more than a phone conversation – this could be an in-person conversation. Not on Valentine’s Day. Find out what his deal is. Let him know that you would like to have him back. Yeah, you did send him mixed messages, but you’re also sending me mixed messages, because you have different long-term goals. You haven’t said anything to me that indicates that your long-term goals are now in alignment with his. So, you can’t have him back just to have him back, because otherwise you’ll be getting into the same rut you were in — that you don’t have long-term goals in common, which are deal-breakers.
Call him. Talk to him. This needs to be an in-person conversation. Don’t forget to use a little mascara. Don’t forget to use a little lip balm. You don’t want to do a full face of makeup like you’re trying to impress him or something, but this is the day you want to look so damn pretty. You don’t want to look like you’re trying hard. It’s not the day to wear your tightest jeans; it’s not the day to do the most, as they say. And have the conversation in person. Don’t cry, but look cute as hell. T-shirt, leggings, Uggs — but just the way you rock it. Effortless.
This interview has been edited and condensed.