Should I Have Doubts After This Date?

So I’ve had a guy friend and he’s told me he has feelings for me, but when we went out he took me to a place where I know he’s taken other girls. Should I be a little skeptical because I don’t want to be nosey or too over protective and pass any boundaries, but I also don’t want to get hurt.


Dear Anonymous,

It’s hard to trust someone else and hope that that person has good intentions, especially when it’s someone of the opposite sex who you make like. This is true for guys and girls. Guys are often all lumped together because of the mistakes that some guys make, but they aren’t all bad. Yes, there are some who are players and cheaters and liars and fakes. But, the same can be said about girls. If you’ve been hurt before it can be even harder to try to open yourself up again. It sounds like that may be the case, or this guy has a reputation of some kind, which has made you worry a bit from the start.

It’s smart to be a bit cautious in the beginning, but you describe him as your “friend” and yet you’re unsure about his intentions after the first date. I think that is something to think about more than where you went on your date. If don’t have a good feeling about getting romantically involved with this guy, then think about why that is. Base your feelings on examples that add to that uneasy feeling. If you can’t come up with any solid reasons why you should be worried, then continue to get to know him better as more than a friend and see how it goes.

For all you know, he may have taken you there because he likes that place and knows it’s consistently good. Maybe he didn’t want to have to worry about trying something new with you. He probably doesn’t know that you know he’s taken other girls there. If he would’ve known that, maybe he would’ve taken you somewhere else. I get that you don’t want to be treated like “just another girl.” No girl wants that. But we also can’t expect a guy to take us somewhere really special for our first date because that’s normal to see in chick flicks. That being said, if you were to specifically ask to go on a date to some new place he’s never been or never taken anyone before, and he agrees but then fails by simply ordering pizza while watching some show he knows you hate–well that would be a definite red flag. Even in a case like that, it’s not about where you are or what you’re doing (pizza and cuddling on the couch can be fun with a good show or movie); it’s about how you guys are communicating and the effort you both put into it. If you feel like he didn’t put much effort into the date, then it’s fine to be a bit bummed. But ask yourself what happened on that date for the real answers about whether or not you should be skeptical now. 

1. Did he ask you questions to get to know you better and did you ask him questions?

2. Did he listen to you while you were talking or was he texting the whole time or just checking you out repeatedly? (There’s nothing wrong with some visual attention, as long as you’re cool with it, and his eyes aren’t glued to your chest the entire time you’re talking.) Can you say that you honestly listened to him as well?

3. Did you have a good time and feel comfortable around him? It’s okay to be nervous, but if you felt uncomfortable at any time by comments he made or if he was too touchy feely for your taste, then those would be red flags.

In the end, it can really go either way as far as his intentions. However, it’s good that he said he has feelings for you to show that he’s being straightforward from the start. That can be hard to say, especially when you’re already friends. Try to be upfront with him, too. If you can now think of specific things he said or did that worry you, but they aren’t huge issues, then it’s okay to see where this goes. But, tell him if something really bothered you. If you felt like he was looking more for an easy way to get some action and you want a relationship, then call it quits and go back to being friends (or not–up to you). Telling someone exactly what’s on your mind may sound scary, but it’s so much better than acting fine when you’re really not. Plus, you don’t want to start something that could potentially be great by playing games or being even a little bit fake with him.

It all comes down to how you answer the questions I posed to you and what you feel is best to do about it. We can’t always know someone’s intentions, but we can look at the facts, tell them exactly how we feel (to save time and prevent drama), and try to enjoy the rest.

Now that I’ve said what I think, what do YOU think? 


What do YOU think?

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