Demystifying Dating Part 2: Answers to Your Dating Questions From 5 Real Women

A few weeks ago, I published a blog post all about dating and relationships- Do You Follow “The Rules”? Getting Real About Dating. After hitting publish, I was flooded with comments, emails and tweets. It appears that everyone has an opinion or story when it comes to this hot topic. (I know I certainly do)

Last week, we heard from the men…five real dudes opened up and answered YOUR most pressing questions about first dates, online dating, text messages, making plans, becoming exclusive, who pays on dates, who should make the first move and so much more.

To keep things fair and balanced, today, we hear from the ladies. Meet five, six ladies who are spilling it all when it comes to dating and relationships. (These ladies are all my personal friends- obviously, I can personally vouch that they are all amazing women)

These questions were compiled by a panel of about four dudes (some who participated in last week’s post) along with questions I came up with myself.

Here’s what ladies are really thinking when it comes to dating and relationships…read on.

Meet The Ladies

demystifying dating- Jessica Lawlor

Say hello to…Lindsey, age 33 from Hatboro, PA
Relationship Status: Married (Fun fact: Lindsey is married to Jason from the dudes post last week)

Say hello to…Kelsie, age 29 from Oreland, PA
Relationship Status: Single

Say hello to…Julia, age 29 from Hatboro, PA
Relationship Status: In a relationship

Say hello to…Brittany age 27 from New York, NY
Relationship Status: Single

Say hello to…Jade, age 26 from Philadelphia, PA
Relationship Status: In a long-term relationship (co-habitating, too)

(Bonus answers come from a friend who preferred to remain anonymous. You’ll see her responses below under “Anon.”)

Say hello to…Anonymous Female, age 29 from Montgomery County, PA
Relationship Status: Married

Let’s get to the questions! Here we go.

1. How do you typically meet guys? (Apps like Tinder or Hinge, online dating site like OKCupid or eHarmony, through friends, at a bar, etc.)

Lindsey: Through friends or at work. Jason and I met at work.

Kelsie: I typically meet guys online, though have had some in person connections at events and through friends. I find the online dating scene to be tiring at times, spending a lot of time trying to connect with people and sometimes not having the time investment ever materialize into an actual date.

Julia: Because I’m not much of a drinker, I don’t spend a whole lot of time at the bar and found that I was rarely meeting new people. So, for several years I dabbled with online dating, mostly using sites like OKCupid and Match. I found success using both sites, liking OKCupid a little better than Match. Match had more requirements and OKCupid gives you the freedom to complete your profile in as much or as little detail as you like- which can sometimes (but not always) tell you how seriously someone is looking to find a relationship. I very briefly tried out Tinder, but I like to see a profile with more detail, like what you would find on Match or OKC, so it wasn’t for me. I met a few great guys online, but it never resulted into a super seriously relationship, usually only dating for about 3-6 months. I met my current boyfriend through yoga 🙂

Brittany: In the past, I’ve met guys at school or through friends. Now it’s a little harder and I have to really dedicate time to put myself out there.

Jade: I have to be honest after college, I was working at an intense agency with long hours and high demands… I gave up on dating! I felt like after the toxicity of dating in college I just needed to figure myself out before committing to someone else and be in a relationship. I tried OkCupid once at the end of 2011, gave up quickly, and then I tried again at the end of 2012. Luckily, my boyfriend was on OkCupid at the same time, we went on a hilarious first date and the rest is history!

Anon: Through friends, or at a bar. Met my husband at a bar.

2. What’s the best way for a guy to get your attention on an online dating site? What about offline?

Lindsey: Eye contact and smile!

Kelsie: On an online dating website, send me a message that isn’t generic and lets me know you are interested in something I said on my profile and ask a thoughtful question.  Offline, eye contact is great for getting a girl’s attention and then just strike up a conversation.

Julia: Dating men online, I always found myself having the best conversations with the men who would reference something from my profile…indicating that they actually read it and showing that we share something in common. The men who would send me a message saying something like, “you’re pretty. how are you?” were usually ignored or deleted. The same would go for offline dating as well. Don’t tell me that I’m pretty and expect me to go on a date with you. Let’s talk about something real and see what we have in common.

Brittany: Be yourself. I don’t want a guy to try and be someone else. If I’m at a bar watching a game or out doing some sort of activity, strike up a conversation related to what I’m doing. I’ll be more inclined to focus my attention on you and keep the conversation going.

Jade: Online, I was looking for similar things in common (going to concerts, Philadelphia Sports Team, craft beer) that way when I would attempt to message someone I could ask them about one of those topics. Offline, if a guy exuded confidence, was polite and made me laugh that always got my attention.

Anon: Have never used a dating site. Offline? Talk to me. You have nothing to lose by making the first move and opening a conversation with someone.

3. What are you most nervous about when you go on a first date?

Lindsey: Saying something stupid, talking too much, making a bad impression.

Kelsie: That we won’t have anything to talk about.

Julia: I’m not much of a nervous person when it comes to dating, especially on a first date. I want to be myself and if someone doesn’t like me for that, I can accept that!

Brittany: When I first meet people, I’m quiet until I’m comfortable. I’ve had a number of guys tell me that I’m shy, which isn’t the case at all. I just need to warm up to a person first.

Jade: I felt like Scott (my boyfriend) and I had great communication the week prior to our first date, I think that I was just nervous that it was all too good to be true! Also, our first date was during a giant snow storm so….the anticipation of rescheduling was there, ha!

Anon: Oversharing. When I get nervous, or meet someone new, I talk…a lot.

4. What is the number one thing a guy can say/do to ruin a first date?

Lindsey: Talking about himself too much, not seeming interested enough in me, talking politics or religion. I guess that’s more than one…LOL!

Kelsie: Disrespect our time. So my advice to this would be: plan the date in advance, follow through the night before with a text confirming your date plans (we really like this) and be there on time.

Julia: I (thankfully) haven’t been on a lot of bad dates, but one thing that has been date ruiner is when a guy is rude to the waitstaff at a restaurant or a bar. Huge turn off.

Brittany: If a guy is rude or brings up sensitive subjects that usually spark serious debate, I’ll lose interest.

Jade: I went on a double date and my date didn’t speak and I had to force the conversation. Eventually, I gave up and knew this was never happening again.

Anon: Talk about an ex. There is a place and time in dating and a relationship where you talk about former relationships, but a first date should be about learning more about each other, not the last person you dated. Unless specifically asked about your last relationship I wouldn’t bring it up. Even if asked, maybe keep the details to a minimum.

5. What annoys or confuses you most about men when it comes to dating?

Lindsey: The games they play… they like you, but they act like they don’t. Their “rules”, which they always end up breaking anyway. You never really know where they stand.

Kelsie: When a date goes great, you get really excited about the guy, and then it all fizzles.

Brittany: Guys who will start a conversation but then disappear. Most of the time it’s the guy who starts the conversation so why start something if you’re not going to finish it? I mean if you’re not interested, just be honest.

Jade: I have experienced this and I know my girlfriends still do. When you think you hit it off with someone and then the guy falls off the face of the earth. Another thing that really annoys me is telling me/friends that you want to make plans and then it never happens. I think if more guys were up front about not wanting to continue the relationship, romantically or not, it would be a lot less frustrating.

Anon: I never liked the games. I was very open about whether or not I was interested in someone, and honestly would appreciate the same. If I like you, I’ll let you know. If I’m not interested, there’s a decent way to say thanks, I’m flattered, but I’m not interested. Don’t just ignore someone, it’s rude.

6. Do you have a timeline for how dates should progress?

Lindsey: No, every situation is different.

Kelsie: I definitely like to keep first dates at a public place and prefer to meet a guy. I usually don’t let a guy pick me up until the 3rd date or hang out at home. It’s a security thing! If I get to this point, it means that I trust you.

Julia: No, I like to see them progress organically. In my experience, it’s been different for every relationship.

Brittany: Not really. I don’t think anything should be forced and it should all just flow naturally.

Jade: Nope! Scott asked me to be his girlfriend after two weeks of dating. I was shocked! I had in my head this plan of how I thought our timeline of dating would go and when that didn’t happen, I embraced the change.

Anon: Nope. Met my husband. Saw him the next night for our first date, our second date the night after that, and the third, the night after that. If you like someone or are interested in seeing them again and your schedules work out, go out, see them again, do what feels natural. Don’t worry about timelines. Conversely, don’t think that just because someone has something already scheduled they are dodging you. They may be a person who likes to honor the commitments they have already made, which is not a bad thing.

7. Who should make the first move? Does it matter?

Lindsey: The guy should. Definitely the guy!

Kelsie: I like when the guy makes the first move.  I don’t think it matters, it’s just personal preference.

Julia: It doesn’t matter.

Brittany: I’m the worst at making a move, so I’d definitely prefer the guy to make a move.

Jade: I don’t think it matters!

Anon: Doesn’t matter.

8. Dating vs. “Couple.” What is the appropriate number of dates before bringing up the idea of exclusivity? If there’s not a “set” amount, what are the signs to look for? How should a guy approach this subject at all without sounding like a possessive crazy person?

Lindsey: There’s no set “number of dates.” I think once sex gets involved, things should be exclusive. But I’m also a serial monogamist, so I tend to fall into relationship mode pretty fast.

Kelsie: I don’t think there’s a set amount of time, but rather an intensity of feelings. I’ll base my feelings on how excited I am to see a guy and how much time I spend thinking about him. I have trouble bringing up this issue for fear of rejection, but ultimately bringing it up helps me feel more secure knowing we are on the same page. Guys are probably equally perplexed of how best to approach the subject, but the best way is just saying flat out you want to have that title of boyfriend/girlfriend and however it comes out, cheesy or serious, we will appreciate it.

Julia: Like I said above, I think this happens organically. You may go on 6 dates with one guy over two weeks and things would naturally progress faster than if you went on 6 dates with one guy over 6 weeks. I think it’s important to express your interest in the person by saying things like, “I like you” or “I like spending time with you.” I also think it’s important to talk about what you want by saying things like “I want to be in a relationship, eventually get married, have kids” or whatever. Put your cards on the table. If the person you are dating never wants kids, you should talk about that. It could be a deal breaker. Don’t waste each other’s time because you are afraid to talk about the things that are important to you.

In all honesty, when a girl or guy calls the person they are dating “crazy” or says things like “they are moving too fast,” I think it means they aren’t that interested in them. When you really like a person and they are talking about marriage, and you want to get married one day, it’s music to your ears!

Brittany: Similar to the timeline question, I think the idea of exclusivity should come up when it feels right. Don’t force a relationship, but if you’re spending a lot of time with someone (dates and just staying in) and talking on a regular basis, I’d say things are getting serious and it should be brought up. A guy should be direct when bringing it up. Let a girl know that you’ve enjoyed spending time together and want to take things to the next level and let her know you don’t want to force her into something if she’s not ready.

Jade: Well, I used to never get past date three, which I took as a sign that the guy didn’t like me enough to even bother dating. (I don’t think Philly is the easiest city to date in.) Then when I met Scott, I just felt like our dates and time together just felt so natural like I had known him for longer than a few weeks. Our communication was consistent and when we started to try and see each other during the work/school week, it made me feel great that someone wanted to hang out with me and enjoyed our time together. As I said before we were officially boyfriend and girlfriend after two weeks of dating. I know this isn’t the timeline for everyone, but when you know, you know.

Anon: There is no set number. Maybe if you feel you’d like to be exclusive offer the info that you aren’t seeing anyone else to open the conversation and see how it’s received. Generally I feel if you are intimate with someone, there is an expectation of exclusivity, but I know not everyone shares that opinion.

9. Exes- should guys pretend they don’t exist or is it OK to acknowledge them when relaying stories about the past? 

Lindsey: They absolutely exist! It’s ridiculous to think that your past can be ignored. Everything that’s happened in your life shapes who you are now and if the guy wants to really know you, he should appreciate your past. But you also shouldn’t shove it down his throat, no need to have every story involve your ex.

Kelsie: Past relationships are part of what shapes your current mindset about dating and I feel it’s necessary to discuss successes and failures. You learn something from every experience, so by talking you can get on the same page with what you want from a relationship, reflecting on past ones of what you what worked or didn’t. I think it’s appropriate to bring up an ex here or there in the context of a story, but too much ex talk can be overkill.

Julia: I think it’s great to talk about past relationships, especially in terms of feelings (i.e. how you felt about the relationship, why things went south, etc.). However, maybe it would be less appropriate to talk about the intimate details of past relationships.

Brittany: Definitely shouldn’t bring up exes too early in a relationship but they should be acknowledged at some point. I guess if someone is getting out of a multi-year relationship and the new person is moving kind of fast, bring it up if you’re feeling rushed. It takes awhile to really move on from someone you were with for a significant amount of time.

Jade: Exes are exes for a reason. I think in the beginning of a relationship its fine to discuss the past, however at a certain time, the cord needs to be cut on this conversation. I don’t think you can move forward and into a healthy relationship if the past is brought up. I personally do not speak about any of my past relationships because I feel like the relationship and partner I have always wanted, I now have. There is no reason to bring up the past when I can be present and work towards the future.

Anon: Refer back to earlier answer…there’s a time and place to discuss these things. They are definitely people who played a defining role in your life. It’s okay to talk about them, just not maybe on a first date and not constantly comparing your new interest or significant other to your ex(es).

10. How easy is it for you to go into a new relationship without bringing past “baggage” into the new situation/relationship?

Lindsey: Difficult! But back to my previous answer… your life experiences shape who you are and that’s just life. I don’t think anyone can say they don’t carry something

Kelsie: When I end a relationship, I make clean breaks with the person to avoid bringing in the baggage.  I try not to get into a new relationship until I feel I’ve let go of any issues associated with a past relationship.

Jade: I think I can go into a new relationship without bringing up any “baggage” until the conversation naturally comes up. I think the “baggage” discussion between two people allows you to say what you would have done differently and what you would now expect from the person you are in a relationship with.

Anon: Depends on the baggage and how fresh it is.

11. Is it weird if a guy shaves his chest?

Lindsey: Yes! Super weird. Trimming is okay, but full on shaving is weird. Embrace who you are. And if you really hate your hairy chest, get laser hair removal. But shaving leads to stubble, which is itchy and no one wants to get close to that.

Kelsie: Manscaping your chest is fine by me, just please don’t shave your legs or arms!

Julia: I prefer a little manscaping. No need to get laser hair removal, but I definitely prefer tamed body hair.

Brittany: It’s not weird if a guy shaves his chest but I do like a little bit of hair. I should mention that I HATE when a guy has too much hair. You’ve gotta maintain it just a little bit.

Jade: Nope!

Anon: Yes and no. depends on what the chest hair looks like.

12. Do you have any dealbreakers?

Lindsey: No. I don’t like to set rules ahead of time. I like to feel out the situation and see where it goes. You might miss out on something spectacular if you count someone out for one little thing. And besides, women are always changing their minds anyway, right? What you set as a “dealbreaker” today might be something you end up liking down the line.

Kelsie: Have a job and a healthy lifestyle, believe in some higher power (no agnostic or atheism), and don’t smoke. I know it’s surface level, but I take height into consideration, preferring the guy to be taller than me.

Julia: Cigarette smokers…gross. Someone who is racist. I am generally more attracted to a person if they have a healthy, active lifestyle, however, just because I am vegan and do yoga does not mean I will not go on a date with someone who eats meat and never works out. But shared interests are definitely important… 🙂

Brittany: Guys who try too hard, are too into fitness and still think they’re in college. Be yourself, don’t judge me if I go for a third slice of pizza and learn how to drink without blacking out.

Jade: If there is a lack of communication, see you never. My time is valuable.

13. Do you play any “games” when it comes to dating? For example, do you think about how long you should wait to text a guy back?

Lindsey: No games. Games are for children. Say what you think, when you want to, and don’t worry so much about it.

Kelsie: Sometimes I’ll wait to text a guy back, and in the beginning few dates, I won’t accept dates arranged on the day of (meaning asking to go out that night).  I do try to restrict timing on a first date just to have an easy out just in case.

Julia: Not usually….but I am probably guilty of this in the past.

Brittany: I don’t play games, but I’m sure it comes off that way. When a guy texts me I usually freak out because I may not know what to say next. That’s about the time I text five girlfriends for advice.

Jade: I know I have fallen victim to the game, but I never saw a need to play them.

Anon: No, if you like me, text me, better…call me. I don’t care when or how soon.

14. Do you believe in dating rules? (Like in my blog post and the book I read) If so, what rules?

Lindsey: No rules! Just go with it and see where it takes you.

Kelsie: I think some have validity as guidelines, but every person and situation is unique. There is not a set recipe for how to have a successful dating experience.

Brittany: I read your post on dating rules and while I don’t really believe in them too much, ladies, don’t play hard to get and never change your appearance for a guy. I think those are the dumbest “rules” ever!

Jade: My dating rule is open communication. I feel like I had nothing to hide from Scott when we were starting our relationship and now that we are over 2.5 years (plus living together), I still feel that way. Our open communication has allowed both of us to express ourselves, tackle tough issues, celebrate the happy moments and build trust.

Anon: No- games, rules, don’t apply to dating. If you are honest and you like someone, all bets are off. Imagine you start dating someone who is “following the rules” to “get someone.” All of a sudden they decide that after four months or more they’ve got you and they don’t have to worry about the rules anymore. They let their guard down and you don’t like this new person. It is not the person you knew at all…enter another failed relationship. If you are yourself from the beginning and you say ‘this is me take it or leave it’, they either like you or don’t and don’t waste your time.

15. How long do you think you need to be in a serious relationship before you come to the conclusion you could spend the rest of your life with that person?

Lindsey: A week? Why waste your time in a “serious relationship” if you don’t know where it’s going. Or worse, if you know it’s not going anywhere. Jason and I might be a bad example of this though… we definitely fast-tracked our relationship. Kissed. A week later spent the weekend together 😉 A month later, moved in together. And a year later, got married.

Kelsie: Tough question!  I haven’t ever experienced that conclusion still being single, but I would imagine a year or two.

Brittany: Well in my last relationship, I thought after about a year I could spend the rest of my life with him. Clearly given my single status that is no longer true.

Jade: I think this could happen at any time when you are in a serious relationship. For me, I think Scott and I were dating for almost three months and we were talking about how one day we both wanted to be parents. In that moment, I knew he was the one for me. Maybe for other people anywhere from 6-12 months you figure out if you can see yourself as long term with your significant other.

Anon: He told me he loved me on our third date (refer back to earlier answer…four days into dating) – I knew date one. He brought pizza and Bud Light Lime to my shore house and we watched a Phillies game. It wasn’t fancy or expensive – but he showed that he listened to me while we had walked and talked the night before. He listened and he already understood me.

16. Do you believe in true love?

Lindsey: Of course. But it doesn’t mean the relationship won’t need work to maintain. You can find your soul mate and still have to fight to keep it all together. Love doesn’t make a relationship. The work you put into it does.

Kelsie: I do. I have definitely seen other relationships to know it exists, and someday I’ll find it too.

Julia: Yes.

Brittany: Ehh, not really.

Jade: Yes!

Anon: Yes.

17. Did anything surprise you about the guys responses? Or conversely, what made absolute sense to you about their responses?

Lindsey: I was surprised they said they believe in dating “rules.” Totally goes against what I’ve seen, either through personal experience or just talking to my guys friends about it. It would be refreshing if I thought it was true.

Kelsie: I was definitely surprised at the guys’ frustration about women when dating, and the qualities they attributed to us. It hurts to be generalized by our gender as fickle, dishonest and fake. On the contrary, my frustration about dating was answered and completely made sense. If a date went well and you’re almost certain that there should be another date, but then get no follow through, the guy either has other things going on or is trying to keep you on the backburner, which was a word two guys used to describe the situation.

Julia: It was great to read about how most of the guys like an aggressive woman. I tend to be more on the aggressive side so it’s nice to know that my aggressive behavior is generally not a turn off.

Brittany: I was surprised to read that guys also confer with their friends when it comes to texting a girl back. It was refreshing to know that it’s not a weird thing to do.

Jade: It was refreshing to see that guys get just as confused on dating as we do! 

Thank you SO much to my panel of lovely ladies for taking the time to share your innermost thoughts on dating and relationships.

What do you think? Dudes- do any of these responses surprise you? Ladies- are these thoughts in line with your thinking? Leave your thoughts in the comments below.

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  • These posts have been very interesting, Jessica! I’ve had my fair share of dating and dealing with all the feelings and unspoken processes/habits in the last couple of years. It’s funny to read a response and think “that’s happened to me too!” I finished the book ‘Modern Romance’ recently and I think you would find it really interesting. It discusses dating in today’s world of technology and choices; it’s fascinating!

    • Thanks so much, Anita!

      OMG- too weird! I’m actually reading Modern Romance right now and I am LOVING it- much better representation of the world of dating than the book I originally read. Thanks for the recommendation!

      • Awesome! Can’t wait to hear what you think of the book overall. I got tons of insights from reading it.

        • Finished it this weekend and LOVED IT! Debating if I’m going to do another dating post here to talk more about it.

          • Yay! I think the book brings to light many positive points that aren’t really talked about. For example, the point about giving someone more than one date to get to know him/her better. Maybe you could write a follow-up post about what you’ve learned from all your readings and discussions and maybe include how it’s affected your dating life?

          • GENIUS IDEA!

  • Obviously a question about chest hair belongs here. hahaha. Good stuff. I feel like the ladies represented us well!

    • Haha, hey! I put it out there to dudes and someone asked 🙂 Valid question. It appears that manscaping is the way to go.

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